An analysis of the isomerization energies of 1,2-/1,3-diazacyclobutadiene, pyrazole/imidazole, and pyridazine/pyrimidine with the turn-upside-down approach

Majid El-Hamdi, William Tiznado, Jordi Poater, Miquel Solà

Resultado de la investigación: Article

33 Citas (Scopus)

Resumen

The isomerization energies of 1,2- and 1,3-diazacyclobutadiene, pyrazole and imidazole, and pyridazine and pyrimidine are 10.6, 9.4, and 20.9 kcal/mol, respectively, at the BP86/TZ2P level of theory. These energies are analyzed using a Morokuma-like energy decomposition analysis in conjunction with what we have called turn-upside-down approach. Our results indicate that, in the three cases, the higher stability of the 1,3-isomers is not due to lower Pauli repulsions but because of the more favorable σ-orbital interactions involved in the formation of two C-N bonds in comparison with the generation of C-C and N-N bonds in the 1,2-isomers.

Idioma originalEnglish
Páginas (desde-hasta)8913-8921
Número de páginas9
PublicaciónJournal of Organic Chemistry
Volumen76
N.º21
DOI
EstadoPublished - 4 nov 2011

Huella dactilar

Isomerization
Isomers
Decomposition
imidazole
pyrazole
pyrimidine
pyridazine

ASJC Scopus subject areas

  • Organic Chemistry

Citar esto

@article{6890fdf8e2c547dcb978b11c739fd43d,
title = "An analysis of the isomerization energies of 1,2-/1,3-diazacyclobutadiene, pyrazole/imidazole, and pyridazine/pyrimidine with the turn-upside-down approach",
abstract = "The isomerization energies of 1,2- and 1,3-diazacyclobutadiene, pyrazole and imidazole, and pyridazine and pyrimidine are 10.6, 9.4, and 20.9 kcal/mol, respectively, at the BP86/TZ2P level of theory. These energies are analyzed using a Morokuma-like energy decomposition analysis in conjunction with what we have called turn-upside-down approach. Our results indicate that, in the three cases, the higher stability of the 1,3-isomers is not due to lower Pauli repulsions but because of the more favorable σ-orbital interactions involved in the formation of two C-N bonds in comparison with the generation of C-C and N-N bonds in the 1,2-isomers.",
author = "Majid El-Hamdi and William Tiznado and Jordi Poater and Miquel Sol{\`a}",
year = "2011",
month = "11",
day = "4",
doi = "10.1021/jo201639k",
language = "English",
volume = "76",
pages = "8913--8921",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "21",

}

An analysis of the isomerization energies of 1,2-/1,3-diazacyclobutadiene, pyrazole/imidazole, and pyridazine/pyrimidine with the turn-upside-down approach. / El-Hamdi, Majid; Tiznado, William; Poater, Jordi; Solà, Miquel.

En: Journal of Organic Chemistry, Vol. 76, N.º 21, 04.11.2011, p. 8913-8921.

Resultado de la investigación: Article

TY - JOUR

T1 - An analysis of the isomerization energies of 1,2-/1,3-diazacyclobutadiene, pyrazole/imidazole, and pyridazine/pyrimidine with the turn-upside-down approach

AU - El-Hamdi, Majid

AU - Tiznado, William

AU - Poater, Jordi

AU - Solà, Miquel

PY - 2011/11/4

Y1 - 2011/11/4

N2 - The isomerization energies of 1,2- and 1,3-diazacyclobutadiene, pyrazole and imidazole, and pyridazine and pyrimidine are 10.6, 9.4, and 20.9 kcal/mol, respectively, at the BP86/TZ2P level of theory. These energies are analyzed using a Morokuma-like energy decomposition analysis in conjunction with what we have called turn-upside-down approach. Our results indicate that, in the three cases, the higher stability of the 1,3-isomers is not due to lower Pauli repulsions but because of the more favorable σ-orbital interactions involved in the formation of two C-N bonds in comparison with the generation of C-C and N-N bonds in the 1,2-isomers.

AB - The isomerization energies of 1,2- and 1,3-diazacyclobutadiene, pyrazole and imidazole, and pyridazine and pyrimidine are 10.6, 9.4, and 20.9 kcal/mol, respectively, at the BP86/TZ2P level of theory. These energies are analyzed using a Morokuma-like energy decomposition analysis in conjunction with what we have called turn-upside-down approach. Our results indicate that, in the three cases, the higher stability of the 1,3-isomers is not due to lower Pauli repulsions but because of the more favorable σ-orbital interactions involved in the formation of two C-N bonds in comparison with the generation of C-C and N-N bonds in the 1,2-isomers.

UR - http://www.scopus.com/inward/record.url?scp=80055100771&partnerID=8YFLogxK

U2 - 10.1021/jo201639k

DO - 10.1021/jo201639k

M3 - Article

C2 - 21951155

AN - SCOPUS:80055100771

VL - 76

SP - 8913

EP - 8921

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 21

ER -