Nitro ⇌ aci-Nitro Tautomerism

Koop Lammertsma; Bharatam V. Prasad

doi:10.1021/ja00059a032

Nitro ⇌ aci-Nitro Tautomerism

Koop Lammertsma, Bharatam V. Prasad

University of Alabama at Birmingham

Research output: Contribution to journal › Article › peer-review

67 Citations (Scopus)

Abstract

The nitromethane ⇌ aci-nitromethane tautomerism is studied by high-level ab initio methods. The MP2/6-31G* geometry of nitromethane compares well with that determined experimentally. The G1 energy difference between the two tautomers amounts to 14.1 kcal/mol in favor of nitromethane. The calculated heat of atomization of −570.7 kcal/mol for nitromethane differs by only 2.4 kcal/mol from the experimental value. The nitromethide anion has C_s symmetry with the 6-311+G^* basis set. Its G1 proton affinity is 355.2 kcal/mol, which differs from the gas-phase value by 1.4 kcal/mol. The anion does not display Y-aromaticity.

Original language	English
Pages (from-to)	2348-2351
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	115
Issue number	6
DOIs	https://doi.org/10.1021/ja00059a032
Publication status	Published - 1 Mar 1993
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Biochemistry
General Chemistry
Colloid and Surface Chemistry

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10.1021/ja00059a032

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abstract = "The nitromethane ⇌ aci-nitromethane tautomerism is studied by high-level ab initio methods. The MP2/6-31G* geometry of nitromethane compares well with that determined experimentally. The G1 energy difference between the two tautomers amounts to 14.1 kcal/mol in favor of nitromethane. The calculated heat of atomization of −570.7 kcal/mol for nitromethane differs by only 2.4 kcal/mol from the experimental value. The nitromethide anion has Cs symmetry with the 6-311+G* basis set. Its G1 proton affinity is 355.2 kcal/mol, which differs from the gas-phase value by 1.4 kcal/mol. The anion does not display Y-aromaticity.",

author = "Koop Lammertsma and Prasad, \{Bharatam V.\}",

year = "1993",

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T1 - Nitro ⇌ aci-Nitro Tautomerism

AU - Lammertsma, Koop

AU - Prasad, Bharatam V.

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N2 - The nitromethane ⇌ aci-nitromethane tautomerism is studied by high-level ab initio methods. The MP2/6-31G* geometry of nitromethane compares well with that determined experimentally. The G1 energy difference between the two tautomers amounts to 14.1 kcal/mol in favor of nitromethane. The calculated heat of atomization of −570.7 kcal/mol for nitromethane differs by only 2.4 kcal/mol from the experimental value. The nitromethide anion has Cs symmetry with the 6-311+G* basis set. Its G1 proton affinity is 355.2 kcal/mol, which differs from the gas-phase value by 1.4 kcal/mol. The anion does not display Y-aromaticity.

AB - The nitromethane ⇌ aci-nitromethane tautomerism is studied by high-level ab initio methods. The MP2/6-31G* geometry of nitromethane compares well with that determined experimentally. The G1 energy difference between the two tautomers amounts to 14.1 kcal/mol in favor of nitromethane. The calculated heat of atomization of −570.7 kcal/mol for nitromethane differs by only 2.4 kcal/mol from the experimental value. The nitromethide anion has Cs symmetry with the 6-311+G* basis set. Its G1 proton affinity is 355.2 kcal/mol, which differs from the gas-phase value by 1.4 kcal/mol. The anion does not display Y-aromaticity.

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JF - Journal of the American Chemical Society

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ER -

Nitro ⇌ aci-Nitro Tautomerism

Abstract

ASJC Scopus subject areas

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