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

66 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
General Chemistry
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/ja00059a032

Cite this

@article{0c91c4d833834d4bad15c31505b7feea,

title = "Nitro ⇌ aci-Nitro Tautomerism",

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",

month = mar,

day = "1",

doi = "10.1021/ja00059a032",

language = "English",

volume = "115",

pages = "2348--2351",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "6",

}

TY - JOUR

T1 - Nitro ⇌ aci-Nitro Tautomerism

AU - Lammertsma, Koop

AU - Prasad, Bharatam V.

PY - 1993/3/1

Y1 - 1993/3/1

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.

UR - http://www.scopus.com/inward/record.url?scp=0001146205&partnerID=8YFLogxK

U2 - 10.1021/ja00059a032

DO - 10.1021/ja00059a032

M3 - Article

AN - SCOPUS:0001146205

SN - 0002-7863

VL - 115

SP - 2348

EP - 2351

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 6

ER -

Nitro ⇌ aci-Nitro Tautomerism

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this