Measurement of the strain energy of a transient bridgehead imine, 4-azahomoadamant-3-ene, by photoacoustic calorimetry

Wayne, G.; Snyder, Gary J.; Rogers, Donald W.

doi:10.1021/ja00074a087

Cited by 22 publications

(16 citation statements)

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“…The G2-ae estimates for hydrogen azide, azidomethane, and (anti-)azidoethane reproduce those of Rogers and McLafferty (RM) (1995 estimates for azidomethane and azidoethane are more negative than would be predicted on the basis of experimentally derived results for "higher homologous azides" (1-azidoadamantane, 3-azido-3-ethylpentane and 2-azido-2-phenylpropane) (Wayne et al, 1993), they hypothesize that the G2-ae estimates might be too negative. Rice et al (2000).…”

Section: Gas-phase Enthalpies-of-formationsupporting

confidence: 56%

“…Some were considered "preliminary" (Murrin and Carpenter, 1957) or "approximate" (Lee et al, 1989) by the authors who published it. Some were not subject to peer review (Thompson, 2000); or if found in a peer-reviewed paper, the context suggests that it would have been difficult for a reviewer to judge its merit (Wayne et al, 1993). And even data that appear to meet high standards (Fagley and Myers, 1954;Fagley et al, 1953) have been questioned by others (Evans et al, 1959;Pepkin et al, 1993 ] for "isodesmic reactions" and will be referred to as the "G2-ir" method.…”

Section: Introductionmentioning

confidence: 99%

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Computational Chemistry-Based Enthalpy-of-Formation, Enthalpy-of-Vaporization, and Enthalpy-of-Sublimation Predictions for Azide-Functionalized Compounds

McQuaid¹,

Rice²

2006

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Section: Gas-phase Enthalpies-of-formationsupporting

confidence: 56%

Section: Introductionmentioning

confidence: 99%

Computational Chemistry-Based Enthalpy-of-Formation, Enthalpy-of-Vaporization, and Enthalpy-of-Sublimation Predictions for Azide-Functionalized Compounds

McQuaid¹,

Rice²

2006

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“…3 We observed that cleavage of the N 3 group by hydrogen in reactions similar to reaction ͑1͒ is very exothermic, having a mean ⌬H hyd 298 ϭϪ81.1Ϯ2.0 kcal mol Ϫ1 . The discrepancy between early estimates of ⌬H f and our experimental measurements is nearly 20 kcal mol Ϫ1 .…”

mentioning

confidence: 79%

“…Calculated ⌬H f 298 values for methyl and ethyl azides are also more negative than our results for the higher homologous azides. 3 At present, it is not clear which is dominant among three plausible sources of error: systematic experimental error, lack of correspondence between the lower azides and their higher homologs, or lack of transferability of the HLC correction. 7 It is likely that all three contribute.…”

Section: Error Sourcesmentioning

confidence: 99%

G2 ab initio calculations of the enthalpy of formation of hydrazoic acid, methyl azide, ethyl azide, methyl amine, and ethyl amine

Rogers

McLafferty

1995

The Journal of Chemical Physics

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“…Recent hydrogenation experiments show the enthalpy of hydrogenation of gaseous alkyl azides to be ca. 340 kJ/mol [32]. Assuming this is so for aryl azides as well, and ignoring phase change enthalpies once again results in a value of ca.…”

mentioning

confidence: 97%

Paradigms and paradoxes: organic thermochemistry without hydrogen: carbon oxides and nitrides

Slayden

Liebman

2008

Struct Chem

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All organic compounds contain carbon. Most contain hydrogen. This brief study discusses the enthalpy of formation of a collection of organic compounds containing only oxygen or nitrogen accompanying the carbon.By definition, organic chemistry is the chemistry of carboncontaining compounds. Almost always, in practice organic chemistry is also the chemistry of compounds containing hydrogen. Relatedly, organic thermochemistry discusses the thermochemistry of carbon-, and most often, hydrogen-, containing species. There are several thousand organic species for which the enthalpies of formation is known. In the current note we discuss the enthalpies of formation of those species that lack hydrogen, in particular, carbon oxides and carbon nitrides but not halocarbons. The current study will be limited to those species for which these data are found from experiment, whether or not the species be isolable. We will also limit our attention to neutral species and so ignore all ions such as the commonplace CN -and rather exotic CN + . We proceed first through the oxides and then the nitrides of carbon. Within each group, the compounds are discussed in order of increasing number of carbons, and then by increasing number of oxygens or nitrogens. All unreferenced enthalpies of formation in the current study are taken from Ref.[1] and may tacitly be assumed to refer to gaseous species at 298 K and 1 atm unless otherwise said.While there are a respectable number of species containing only carbon and oxygen, there are only three isolable compounds for which enthalpy of formation data are available: carbon monoxide (CO), carbon dioxide (CO 2 ) and propadienedione (C 3 O 2 ), the so-called carbon suboxide. Not limiting our species of interest by grounds of isolability allows us to consider other oxides of carbon, CO 3 , C 2 O, and C 3 O.Enthalpies of formation of CO and CO 2 are found from numerous sources. We choose the values -110.525 and -393.509 kJ/mol [2]. These values are well-established, the latter providing a benchmark value for the enthalpies of formation and combustion of nearly all organic compounds. Perhaps the only thermochemical observation of consequence we will make in this study relates to their carbon-oxygen bond energies. The ratio of the C-O bond energy in CO 2 to that of (the mean) value for CO is very nearly the same as the ratio for the Si-O bond energies in SiO 2 and gaseous SiO despite the fact that CO 2 is ''naturally'' a gas while SiO 2 is ''naturally'' a solid. Perhaps this is not so strange: this near constant ratio in the gas phase for some other pairs of species containing group 14-16 atoms was first pointed out in Ref. [3], and extended by consideration of experimentally unexplored neutrals [4] as well as valence isoelectronic pairs of cations [5], anions [5], and some hydrogen-containing pentatomics as well [6]. Summarizing, for 10 valence electron AB and 16 valence electron AB 2 , we findThis is a comfortably simple approximation for bond energies and a good example of how the investigation of

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Measurement of the strain energy of a transient bridgehead imine, 4-azahomoadamant-3-ene, by photoacoustic calorimetry

Cited by 22 publications

References 0 publications

Computational Chemistry-Based Enthalpy-of-Formation, Enthalpy-of-Vaporization, and Enthalpy-of-Sublimation Predictions for Azide-Functionalized Compounds

Computational Chemistry-Based Enthalpy-of-Formation, Enthalpy-of-Vaporization, and Enthalpy-of-Sublimation Predictions for Azide-Functionalized Compounds

G2 ab initio calculations of the enthalpy of formation of hydrazoic acid, methyl azide, ethyl azide, methyl amine, and ethyl amine

Paradigms and paradoxes: organic thermochemistry without hydrogen: carbon oxides and nitrides

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