Benzene is unsaturated. For benzene (hypothetically three double bonds) it costs $49.8 / 3 = 16.6$ kcal/mol to hydrogenate each double bond. Answer: Pyridine is less reactive, than benzene toward electrophilic aromatic substitution, because nitrogen is more electronegative, than carbon and acts like an electron withdrawing group.As a result, the meta hydrogen is substituted. How is naphthalene aromatic? Any compound containing an aromatic ring(s) is classed as 'aromatic'. ** Please give a detailed explanation for this answer. From this simple model, the more confined an electron, the higher will be its energy. Why naphthalene is less aromatic than benzene? 2003-2023 Chegg Inc. All rights reserved. The chemical naphthalene is used to make the beta-blocking drug nadoxolol. Results are analogous for other dimensions. criteria, there right? The heat of hydrogenation of benzene is 49.8 kcal mol^-1 while its resonance energy is 36.0 kcal mol^-1 . This contrasts with the structure of benzene, in which all the $\ce{CC}$ bonds have a common length, $\pu{1.39 }$. . Naphthalene has two aromatic rings, but only 10 pi electrons (rather than the twelve electrons that it would prefer). And then right here, Can banks make loans out of their required reserves? The cookie is set by the GDPR Cookie Consent plugin and is used to store whether or not user has consented to the use of cookies. So we have a carbocation So go ahead and highlight those. This means that naphthalene has less aromatic stability than two isolated benzene rings would have. Why is benzene not cyclohexane? Pi bonds cause the resonance. We cannot use it for polycyclic hydrocarbons. But naphthalene is shown to are just an imperfect way of representing the molecule. Stability means thermodynamic stability ie enthalpy of formation . are equivalents after I put in my other shared by both rings. 3. side like that. Notice also that meta-substitution reactions on nitrobenzene are faster than para-substitution reactions because the nitro group is a meta-directing group. The moth balls used commonly are actually naphthalene balls. These cookies track visitors across websites and collect information to provide customized ads. I'm curious why the top carbon of the five-membered ring is sp2 hybridized rather than sp3; with the hydrogen attached, two C-C bonds, and the lone pair it seems like it should be sp3. For example, rings can include oxygen, nitrogen, or sulfur. A simple model for delocalisation is the particle in a box (in this case, more of a rectangle). The cookies is used to store the user consent for the cookies in the category "Necessary". And I have some pi I could move these And the pi electrons W.r.t. Naphthalene is the Personally, I would have used the structure on the left as the electrophile, because it shows explicitly that the sulfur atom is electron deficient. i think you heared wrong as he said that azulene is an isomer of naphthalene ,and i agree because isomers mean that compounds have an equal number of each atom i.e have the same general molecular formula so if you count the number of carbon atoms in both azulene and naphthalene,you will find that they have the same number =10 carbon atom and in the same way with hydrogen atom =8 (C10H8) so they are isomers(azulene& naphthalene) not (anthracene& naphthalene). vegan) just to try it, does this inconvenience the caterers and staff? of 6 pi electrons. So these, these, and The best answers are voted up and rise to the top, Not the answer you're looking for? b) Alkyl groups are activating and o,p-directing. In electrophilic aromatic substitution reactions, naphthalene reacts more readily than benzene. Naphthalene has five double bonds i.e 10 electrons. of finding those electrons. the resulting dot structure, now I would have, let's As you said, delocalisation is more significative in naphthalene. Why reactivity of NO2 benzene is slow in comparison to benzene? The greater acidity of pyrroles and indoles is a consequence of the resonance stabilization . Aromatic hydrocarbons are cyclic, planar compounds that resemble benzene in electronic configuration and chemical behavior. The actual value from NIST (to cis-decalin) is $-318$ kJ/mol, or $-76$ kcal/mol. The cookie is set by GDPR cookie consent to record the user consent for the cookies in the category "Functional". So if I go ahead 1. They are also called aromatics or arenes. what is difference in aromatic , non aromatic and anti aromatic ? It's not quite as It only takes a minute to sign up. There are three aromatic rings in Anthracene. In a cyclic conjugated molecule, each energy level above the first . A white solid, it consists of known household fumigant. carbon has a double bond to it. And so that's going to end Both are aromatic in nature both have delocalised electrons but naphthalene has more resonance structures and more delocalisation so overall it must be more stable for a single ring. Technically , naphthalene has fused rings unlike benzene and thus the two systems are different and cannot be compared. Perhaps the most noteworthy difference between aromatic hydrocarbons and polar organic functionality in terms of drug chemistry is the difference in solubility properties. Why is benzene so stable? Naphthalene is a solid that sublimes at standard atmospheric temperature with the sublimation point at around 80 C or 176 F. At low temperature, its vapour pressure is high enough, 1 mmHg at 53 C, to make the solid form of naphthalene evaporate into gas. A molecule is aromatic when it adheres to 4 main criteria: The naphthalene ion forms unconventional carbon-based ionic hydrogen bonds with H2O and CH3OH (CH +OH2 and CH +OHCH3, respectively) which can be extended to hydrogen bonding chains with additional solvent molecules. It can be very dangerous if moth balls are eaten, so it is especially important that mothballs are stored well out of the reach of small children and pets. Direct link to Navid's post Napthalene is less stable, Posted 9 years ago. It draws electrons in the ring towards itself. expect, giving it a larger dipole moment. Direct link to Mayank Kumar 's post At which position in napt, Posted 9 years ago. explanation as to why these two ions are aromatic. It is best known as the main ingredient of traditional mothballs. And all the carbons turn These catbon atoms bear no hydrogen atoms. those pi electrons are above and below Naphthalene is also planar and has 4n + 2 pi electrons (10) giving it the stabilizing and resonating aromatic properties shared with benzene. F-C acylation can be stopped after one acyl group is added AlCl 3 + R O ClR C O. over here on the right, is a much greater contributor of naphthalene are actually being If a molecule contains an aromatic sub-unit, this is often called an aryl group. Given its larger delocalisation, it seems rational that the energy levels of naphthalene have less energy in comparison to benzene. Generalizations regarding functional groups on benzene ring, The order of aromaticity of benzene, thiophene, pyrrole, furan, and pyridine. Resonance/stabilization energy of benzene = 36kcal/mol. And again in the last video, we The cookie is used to store the user consent for the cookies in the category "Analytics". And azulene is a beautiful Aromatic molecules are cyclic, conjugated, have (4n+2) pi electrons, and are flat. 2)According to resonance theory, naphthalene can be considered a hybrid of three Kekul structures . No naphthalene is an organic aromatic hydrocarbon. We all know they have a characteristic smell. Benzene shows that it is actually unsaturated because it adds hydrogen or chlorine, although only when allowed to react under very vigorous conditions (higher temperature or pressure) compared to those required for alkenes and alkynes. Naphthalene is a nonpolar compound. ions are aromatic they have some The $n$-th energy level for an electron confined in a single dimensional box (line segment) is, $$E_n = \frac{n^2 h^2} {8 m_e L^2}\text{,}$$. Aromatic compounds are chemical compounds that consist of conjugated planar ring systems accompanied by delocalized pi-electron clouds in place of individual alternating double and single bonds. Thus , the electrons can be delocalized over both the rings. In days gone by, mothballs were usually made of camphor. However, there are significant differences that demonstrate that one of the rings is more subject to oxidative and reductive change than is benzene. The reason is that the most favorable resonance structures for either intermediate are those that have one fully aromatic ring. A long answer is given below. -The molecule is having a total of 10 electrons in the ring system. I have edited the answer to make it clearer. Browse other questions tagged, Start here for a quick overview of the site, Detailed answers to any questions you might have, Discuss the workings and policies of this site. If you preorder a special airline meal (e.g. see, these pi electrons are still here. Surfactants are made from the sulfonated form of naphthalene. (Hint: Look at your answers to Problem)Figure: Comparison of heat released by the hydrogenation of cyclohexene, 1,3-cyclohexadiene, and benzene to produce cyclohexane.Problem: Draw all reasonable electron-dot formulas for the nitronium ion (NO2+), the electrophile in . anisole is the most reactive species under these conditions. The chemicals in mothballs are toxic to humans and pets. Does a summoned creature play immediately after being summoned by a ready action? resonance structures. Nitration of naphthalene and anthracene. So there's that 10 pi electrons. Treated with aqueous sodium hydroxide to remove acidic impurities. Why are arenes with conjoined benzene rings drawn as they are? See Answer Question: Why naphthalene is less aromatic than benzene? Short story taking place on a toroidal planet or moon involving flying. For an example: The tricyclic aromatic hydrocarbons anthracene and phenanthrene may be analyzed in the same manner. There are since pi-electrons in this benzene, these pi-electrons are delocalized throughout the whole molecule. This gives us 6 total pi electrons, which is a Huckel number (i.e. It Sigma bond cannot delocalize. solvent that is traditionally the component of moth balls. Please also add the source (quote and cite) that gave you this idea. . In terms of heat of hydrogenation Naphthalene can be hydrogenated to give tetralin . So it's a benzene-like And then going around my How do you ensure that a red herring doesn't violate Chekhov's gun? Why does benzene only have one Monosubstituted product? But opting out of some of these cookies may affect your browsing experience. Required fields are marked *. ring on the left. It also has some other I believe the highlighted sentence tells it all. 5)Naphthalene shows substitution reactions with electrophiles rather than addition reactions , just as benzene. So the dot structures And then these electrons In chemistry, aromaticity is a chemical property of cyclic (ring-shaped), typically planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to saturated compounds having single bonds, and other geometric or connective non-cyclic arrangements with the same set of atoms. The final DCKM consists of . And showing you a little Electron deficient aromatic rings are less nucleophlic. . It can affect how blood carries oxygen to the heart, brain, and other organs. There isn't such a thing as more aromatic. here on the left, I can see that I have However, technically this cannot be considered as a proof as this rule applies ONLY TO MONOCYCLIC compounds. Further hydrogenation gives decalin. highlight those electrons. Molecules that are not aromatic are termed aliphatic. So every carbon to the overall picture of the molecule. Other carbon-carbon bonds have varying bond order, as reflected in the bond lengths shown on the right hand structure. Can somebody expound more on this as to why napthalene is less stable? I exactly can't remember. So if I go ahead and draw the Direct link to Ernest Zinck's post Ordinary single and doubl, Posted 9 years ago. The pyridine/benzene stability 'paradox'? Non-aromatic molecules are every other molecule that fails one of these conditions. compounds is naphthalene. Naphthalene is the simplest polycyclic aromatic hydrocarbon since it is only a bicyclic molecule made up of two aromatic benzenes. An examination of each contributing structure discloses that the carbon#9 to carbon#10 bond has 80% double bond character, whereas the opposite bond across the ring (the carbons are not numbered) has 80% single bond character. Change), You are commenting using your Facebook account. would push these electrons off onto this carbon. charge is delocalized throughout this It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. Acute (short- term) exposure of humans to naphthalene by inhalation, ingestion, and dermal contact is associated with hemolytic anemia, damage to the liver, and neurological damage. As an aromatic hydrocarbon, naphthalenes structure consists of a fused pair of benzene rings. All the carbon atoms are sp2 hybridized. Benzene is an aromatic hydrocarbon because it obeys Hckels rule. organic molecules because it's a throughout both rings. . satisfies 4n+2). On a quick glance you might think that as 10 pi electrons are delocalized on 10 carbon atoms in case of naphthalene, it should have resonance energy per bond similar to that of benzene and thus making both equally active towards electrophiles. and draw the results of the movement of It is a component of coal-tar and the US Occupational Health and Safety Administration classifies it as noncarcinogenic. Thus, benzene is more stable than naphthalene. So, it reduces the electron density of the aromatic ring of the ring. p orbital, so an unhybridized p orbital. That is, benzene needs to donate electrons from inside the ring. Burns, but may be difficult to ignite. The tricyclic aromatic hydrocarbon phenanthrene has substantial resonance stabilization, as shown in the following diagram. Oxygen is the most electronegative and so it is the least aromatic. This cookie is set by GDPR Cookie Consent plugin. top carbon is going to get a lone pair And one way to show that would The solvents for an aroma are made from molten naphthalene. This page is the property of William Reusch. How Do You Get Rid Of Hiccups In 5 Seconds. When naphthalene is metabolized in the liver, oxidative stress induces massive hemolysis, resulting in hemolytic anemia, methemoglobinemia, hemoglobinuria, and jaundice. How to tell which packages are held back due to phased updates. Posted 9 years ago. our single bond, in terms of the probability those electrons, I would now have my pi electrons right there. What is the purpose of this D-shaped ring at the base of the tongue on my hiking boots? They are known as aromatic due to their pleasant smell. This means that naphthalene has less aromatic stability than two isolated benzene rings would have. ( Azul is the Spanish word for blue.) the two rings. People are exposed to the chemicals in mothballs by inhaling the fumes. Extended exposure to mothballs can also cause liver and kidney damage. But if I look over on the right, Benzene and naphthalene are the most refractory aromatic compounds [75], [76]. This patent application was filed with the USPTO on Thursday, April 26, 2018 Therefore, the correct answer is (B). ahead and analyze naphthalene, even though technically we Phenanthrene is more stable than anthracene due to the larger stability of the -system of the former, which is more aromatic. electrons right here. It is thus perfectly reasonable to rationalise that more delocalisation results in more stability. Benzene has six pi electrons for its single aromatic ring. six pi electrons. How to Make a Disposable Vape Last Longer? has a formula of C10H8. Why is the resonance energy of naphthalene less than twice that of benzene? The structure Why chlorobenzene is less reactive than benzene towards electrophilic substitution reaction? Correct option is A) The above given compounds are more reactive than benzene towards electrophilic substitution reaction. Is m-cresol or p-cresol more reactive towards electrophilic substitution? And if Khan has a videdo about it, please refer to me :), It is the strength of the intermolecular forces that determines the volatility of a compound, At which position in napthalene is the carbonation most stable. And if we think about If it is benzene, then how come the heat of hydrogenation of benzene to cyclohexane is an exothermic process which releases energy, indicating that cyclohexane is more stable. the blue region, which is again the rare, especially ring, it would look like this. Naphthalene =unsaturated. A short answer is: you're forgetting that a double bond is shared between the two rings in naphthalene. (1) Reactions of Fused Benzene Rings Thus naphthalene is less aromatic but more reactive . By clicking Post Your Answer, you agree to our terms of service, privacy policy and cookie policy. The redistribution And therefore each carbon has a https://www.facebook.com/madoverchemistry/, electrons are delocalised over both the rings, heat of hydrogenation calculation also show stabilisation, aphthalene has fused rings unlike benzene, Atomic number Atomic mass number Atomic size, Melting point bond dissociation energy & bond energy, https://www.top10homeremedies.com/news-facts/10-hidden-dangers-in-your-home.html. So it's a negative formal Originally, benzene was considered aromatic because of its smell: it has an "aromatic" odor. As seen above , the resonance energy of naphthalene(63kcal/mol) is more than that of benzene(36kcal/mol).So, naphthalene should be more stable than benzene. So I could show those pi The cookie is used to store the user consent for the cookies in the category "Performance". Why is naphthalene less stable than benzene according to per benzene ring? can't use Huckel's rule. show variation in length, suggesting some localization of the double You can see that you have Why benzene is more aromatic than naphthalene? However, some aromatics are also toxic to humans and a contributor to smog when released into the atmosphere. out to be sp2 hybridized. where $m_e$ is the mass of the electron, $h$ is the Planck's constant and $L$ is the length of the line segment. So the correct answer is Option C. Why are naphthalene and anthracene regarded as aromatic compounds? Another example would be One of the five contributing structures has three fused benzene ring moieties, two of the structures have a benzene ring fused to a 10 -electron annulene, and the remaining two are 14 -electron annulenes, which are aromatic by the Hckel Rule. Aromatic compounds are important in industry. Executive summary: The pH of 1,4-Naphthalenedicarboxylic acid at 10% in water is 3.6 (according to OECD 122 and DIN 19268:2007-05). counting resonance structures is a poor way to estimate aromaticity or the energy involved. It is converted to 1-naphthol and 2-naphthol, which can be excreted though the kidney. And one of those Polynuclear aromatic hydrocarbons (PAHs) are compounds containing multiple benzene rings and are also called polycyclic aromatic hydrocarbons. electrons over here, move these electrons Nitration at position 2 produces a carbocation that has 6 total resonance structures, 2 of which appear to preserve the aromaticity of the second ring. delocalized or spread out throughout this another resonance structure. Biomolecular interactions is one area of research that sits in every camp of resolution vs the time required, from the quantum mechanical level to in vivo studies. Naphthalene diimide based polymer acceptor in solar cells deliver high performance owing to the electron transportability.25 Naphthalene is toxic and may cause acute hemolytic anemia.26 Naphthalene is reported to have a larger total aromatic stabilization than benzene but is considered less aromatic than benzene Comments, questions and errors should be sent to whreusch@msu.edu. Notice that nitrobenzene is less reactive than benzene because the nitro group is a deactivating substituent. This $36.0$ kcal/mol may be regarded as a direct measure of aromaticity and is cited in many places as resonance energy. 6 285 . His rule states that if a cyclic, planar molecule has 4n+2 electrons, it is considered aromatic. It occurs in the essential oils of numerous plant species e.g. And in this case, we A short answer is: you're forgetting that a double bond is shared between the two rings in naphthalene. Shouldn't the dipole face from negative to positive charge? Stack Exchange network consists of 181 Q&A communities including Stack Overflow, the largest, most trusted online community for developers to learn, share their knowledge, and build their careers. in organic chemistry to have a hydrocarbon And this resonance structure, Electrophilic aromatic substitution (EAS) is where benzene acts as a nucleophile to replace a substituent with a new electrophile. On the other hand, the hydrogenation of benzene gives cyclohexane. So that would give me electrons are fully delocalized this would sort of meet that first Naphthalene contain 10 electrons. electrons on the five-membered ring than we would All the above points clearly indicate that naphthalene is an aromatic entity too. How does nitration of naphthalene and anthracene preserve aromaticity? Is it suspicious or odd to stand by the gate of a GA airport watching the planes? Based upon global structural searches and B3LYP and CCSD(T) calculations, we present herein the perfectly planar dicyclic boron Huckels rule applies only to monocyclic compounds. Similar perturbations of bond lengths in benzene have been observed as a consequence of angle strain resulting from small fused rings (the Mills-Nixon effect). Direct link to ss loves science's post At 5:10, anthracene is re, Posted 8 years ago. off onto that top carbon. For the Nozomi from Shinagawa to Osaka, say on a Saturday afternoon, would tickets/seats typically be available - or would you need to book? Naphthalene has a distinct aromatic odor. sp2 hybridized. Linear Algebra - Linear transformation question. Experts are tested by Chegg as specialists in their subject area. Every atom in the aromatic ring must have a p orbital. Step 3 Loss of a proton from the carbocation to give a new aromatic compound. So naphthalene is more reactive compared to single ringed benzene. Which is more aromatic benzene or naphthalene? https://www.khanacademy.org/science/organic-chemistry/conjugation-diels-alder-mo-theory/molecular-orbital-theory/v/intro-to-molecular-orbital--mo--theory, http://en.wikipedia.org/wiki/H%C3%BCckel_method, Creative Commons Attribution/Non-Commercial/Share-Alike. have delocalization of electrons across Naphthalene. So, tentative order of reactivity in electrophilic substitution: Nitrobenzene, acetophenone, benzene, toluene, anisole; i.e. Is a PhD visitor considered as a visiting scholar? Why did Ukraine abstain from the UNHRC vote on China? For example, benzene. a naphthalene molecule using our criteria for Thus, it is insoluble in highly polar solvents like water. dyes, aromatic as is its isomer naphthalene? Unlike in case of benzene all pi electrons of naphthalene are not equally delocalized on the 10 carbons. 1 or more charge. In two recent papers, we have presented parameterizations of the SM5.42R universal solvation model for use with density functional theory (DFT) employing the BeckePerdewWang-1991 (BPW91) functional and the MIDI!6D, DZVP, and 6-31G* basis sets and for use with ab initio HartreeFock calculations employing the MIDI!6D basis set . longer wavelength. Naphthalene, as a covalent compound, is made up of covalent molecules only. Three important contributing structures to the resonance hybrid may be drawn, as shown in the following diagram. How would "dark matter", subject only to gravity, behave? Inorganic analogues of hydrocarbons or polycyclic aromatic hydrocarbons (PAHs) are of current interest in chemistry. Camphor for skin Lotions and creams containing camphor can be used to relieve skin irritation and itchiness and may help to improve the overall appearance of skin. Naphthalene has two aromatic rings, but only 10 pi electrons (rather than the twelve electrons that it would prefer). Camphor and naphthalene unsaturated and alcohol is saturated. Other uncategorized cookies are those that are being analyzed and have not been classified into a category as yet. Washed with water. I have a carbocation. Note: Pi bonds are known as delocalized bonds. Edit: As pointed out in the comments, I have made an error in counting the number of pi electrons in napthlene. crystalline solid Naphthalene is a crystalline solid. If we substitute n=2 it satisfies the Huckels rule 4n+2 electron condition. This cookie is set by GDPR Cookie Consent plugin. Why is benzene more stable than naphthalene according to per benzene ring. The larger stability of the former also correlates with its larger aromaticity, despite the difference in aromaticity between the isomers is now smaller. Treatment with methanol alone gives low extraction efficiency although its recovery by crystallization and precipitation of naphthalene is very easy. As discussed So these are just two that this would give us two aromatic rings, only be applied to monocyclic compounds. Both molecules incorporate 10 electrons in a planar fused-ring skeleton. Naphthalene has two aromatic rings, but only 10 pi electrons (rather than the twelve electrons that it would prefer). It's really the same thing. Benzene ,anthracene and phenanthrene are aromatic compound because those compound obey Huckel's rule (4n+2) electrons.But phenanthrene is relatively more stable because of having More resonating structures. To subscribe to this RSS feed, copy and paste this URL into your RSS reader. However, it's not as 1)Naphthalene is planar.Naphthalene has two rings fused together with 10 carbon atoms. Benzene or naphthalene? It has a total of (From Kshitij IIT JEE Online Coaching) Benzene is different because it is a cyclic conjugated molecule. Why naphthalene is less aromatic than benzene? Naphthalene is an organic compound with formula C10H8. How is the demand curve of a firm different from the demand curve of industry? What is the purpose of non-series Shimano components? Direct link to Henry Dikeman's post I'm curious why the top c, Posted 6 years ago. 10 carbons in naphthalene. Learn more about Stack Overflow the company, and our products. But we could think about it as And here's the five-membered Thus naphthalene is less aromatic Benzene has six pi electrons for its single aromatic ring. Can somebody expound more on this as to why napthalene is less stable? How do/should administrators estimate the cost of producing an online introductory mathematics class? in the orange region, which is difficult for most This is due to a solubility of 5.3% methanol in the fuel and a rapid saturation of 6% of naphthalene in methanol [3]. Pi bonds cause the resonance. Stability of the PAH resonance energy per benzene ring. electrons over here like this. right here, as we saw in the example In benzene, all the C-C bonds have the same length, 139 pm. The chemical reactivity of naphthalene is similar to that of benzene, with electrophilic substitution being common. moment in azulene than expected because of the fact -All the electrons are fully delocalized in the ring system of a naphthalene molecule. Stability is a relative concept, this question is very unclear. Naphthalene has two aromatic rings, but only 10 pi electrons (rather than the twelve electrons that it would prefer). What Is It Called When Only The Front Of A Shirt Is Tucked In? And if I look at it, I can see (LogOut/ Benzene, however, is an extraordinary 36 kcal/mole more stable than expected. bit about why naphthalene does exhibit some The electrons that create the double bonds are delocalized and can move between parent atoms. So I can draw another resonance For naphthalene it would be $-76 / 5 = 15.2$ kcal/mol, again very similar. something like anthracene. However, the heat of hydrogenation of naphthalene calculated experimentally is 80 kcal/mol. heat released by hydrogenation of 5 double bonds(naphthalene) should be -28.6 5 So let me go ahead It only takes a minute to sign up. Stability of the PAH resonance energy per benzene ring. Due to resonance in phenol, the ortho and para hydrogens have a higher electron density. As nouns the difference between camphor and naphthalene is that camphor is (organic compound) a white transparent waxy crystalline isoprenoid ketone, with a strong pungent odour, used in pharmacy while naphthalene is a white crystalline hydrocarbon manufactured from coal tar; used in mothballs. rule, 4n plus 2. right here like that. resulting resonance structure, I would have an ion Its fumes discourage insects, which is no doubt why plants with it evolved in the first place. Both are aromatic in nature both have delocalised electrons but naphthalene has more number of bonds and hence more resonance structures and more delocalisation so overall it must be more stable. in naphthalene. What determines the volatility of a compound?

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