A Molecular Orbital Study of Phenylcarbene and Diphenylcarbene

J. J. Dannenberg; Laura K. Vinson; M. Moreno; J. Bertran

doi:10.1021/jo00284a020

A Molecular Orbital Study of Phenylcarbene and Diphenylcarbene

J. J. Dannenberg, Laura K. Vinson, M. Moreno, J. Bertran

Department of Chemistry

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Abstract

The potential surfaces of diphenylcarbene and phenylcarbene, in singlet and triplet states, have been studied by using the AM1 molecular orbital method. The triplet was found to be the ground state in both cases. The energy difference between the triplet and singlet surfaces is calculated to be somewhat higher than that required by a mechanism for reaction of triplet I with methanol via a thermally populated singlet state. The electron affinity of I was calculated to be quite large (43.2 kcal/mol), suggesting the possibility of a mechanism involving electron transfer from methanol to I. The characteristics of suberanyl and suberenyl carbenes were calculated for comparison. © 1989, American Chemical Society. All rights reserved.

Original language	English
Pages (from-to)	5487-5491
Journal	Journal of Organic Chemistry
Volume	54
Issue number	23
DOIs	https://doi.org/10.1021/jo00284a020
Publication status	Published - 1 Nov 1989

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title = "A Molecular Orbital Study of Phenylcarbene and Diphenylcarbene",

abstract = "The potential surfaces of diphenylcarbene and phenylcarbene, in singlet and triplet states, have been studied by using the AM1 molecular orbital method. The triplet was found to be the ground state in both cases. The energy difference between the triplet and singlet surfaces is calculated to be somewhat higher than that required by a mechanism for reaction of triplet I with methanol via a thermally populated singlet state. The electron affinity of I was calculated to be quite large (43.2 kcal/mol), suggesting the possibility of a mechanism involving electron transfer from methanol to I. The characteristics of suberanyl and suberenyl carbenes were calculated for comparison. {\textcopyright} 1989, American Chemical Society. All rights reserved.",

author = "Dannenberg, {J. J.} and Vinson, {Laura K.} and M. Moreno and J. Bertran",

year = "1989",

month = nov,

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doi = "10.1021/jo00284a020",

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pages = "5487--5491",

journal = "Journal of Organic Chemistry",

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TY - JOUR

T1 - A Molecular Orbital Study of Phenylcarbene and Diphenylcarbene

AU - Dannenberg, J. J.

AU - Vinson, Laura K.

AU - Moreno, M.

AU - Bertran, J.

PY - 1989/11/1

Y1 - 1989/11/1

N2 - The potential surfaces of diphenylcarbene and phenylcarbene, in singlet and triplet states, have been studied by using the AM1 molecular orbital method. The triplet was found to be the ground state in both cases. The energy difference between the triplet and singlet surfaces is calculated to be somewhat higher than that required by a mechanism for reaction of triplet I with methanol via a thermally populated singlet state. The electron affinity of I was calculated to be quite large (43.2 kcal/mol), suggesting the possibility of a mechanism involving electron transfer from methanol to I. The characteristics of suberanyl and suberenyl carbenes were calculated for comparison. © 1989, American Chemical Society. All rights reserved.

AB - The potential surfaces of diphenylcarbene and phenylcarbene, in singlet and triplet states, have been studied by using the AM1 molecular orbital method. The triplet was found to be the ground state in both cases. The energy difference between the triplet and singlet surfaces is calculated to be somewhat higher than that required by a mechanism for reaction of triplet I with methanol via a thermally populated singlet state. The electron affinity of I was calculated to be quite large (43.2 kcal/mol), suggesting the possibility of a mechanism involving electron transfer from methanol to I. The characteristics of suberanyl and suberenyl carbenes were calculated for comparison. © 1989, American Chemical Society. All rights reserved.

U2 - 10.1021/jo00284a020

DO - 10.1021/jo00284a020

M3 - Article

SN - 0022-3263

VL - 54

SP - 5487

EP - 5491

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 23

ER -

A Molecular Orbital Study of Phenylcarbene and Diphenylcarbene

Abstract

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