De-aromatizing phosphole

E. Mattmann; Francois Mathey; A. Sevin; G. Frison

doi:10.1021/jo0108156

De-aromatizing phosphole

E. Mattmann
, Francois Mathey
, A. Sevin
, G. Frison

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

Abstract

Quantum-chemical DFT calculations using the B3LYP functionals have been carried out for 1-R-substitued phospholes and some 1-R-substitued 3,4-dimethylphospholes where R = H, Me, Ph, CN, OH, OMe, F, Cl, and Br. The aromaticity of the phospholyl rings is interpreted as a function of geometric, magnetic, and energetic indexes. It is shown, in agreement with previous experimental results, that phosphole aromaticity does not correlate with pyramidality at phosphorus. Variation of hyperconjugative and to a lesser extent, conjugative effects is responsible for the change in cyclic delocalization for the phospholes studied here.

Original language	English
Pages (from-to)	1208-1213
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	67
Issue number	4
DOIs	https://doi.org/10.1021/jo0108156
Publication status	Published - 22 Feb 2002
Externally published	Yes

Access to Document

10.1021/jo0108156

Cite this

@article{aa9bc6406fe44cd6b6f28353e81955a5,

title = "De-aromatizing phosphole",

abstract = "Quantum-chemical DFT calculations using the B3LYP functionals have been carried out for 1-R-substitued phospholes and some 1-R-substitued 3,4-dimethylphospholes where R = H, Me, Ph, CN, OH, OMe, F, Cl, and Br. The aromaticity of the phospholyl rings is interpreted as a function of geometric, magnetic, and energetic indexes. It is shown, in agreement with previous experimental results, that phosphole aromaticity does not correlate with pyramidality at phosphorus. Variation of hyperconjugative and to a lesser extent, conjugative effects is responsible for the change in cyclic delocalization for the phospholes studied here.",

author = "E. Mattmann and Francois Mathey and A. Sevin and G. Frison",

year = "2002",

month = feb,

day = "22",

doi = "10.1021/jo0108156",

language = "English",

volume = "67",

pages = "1208--1213",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

number = "4",

}

TY - JOUR

T1 - De-aromatizing phosphole

AU - Mattmann, E.

AU - Mathey, Francois

AU - Sevin, A.

AU - Frison, G.

PY - 2002/2/22

Y1 - 2002/2/22

N2 - Quantum-chemical DFT calculations using the B3LYP functionals have been carried out for 1-R-substitued phospholes and some 1-R-substitued 3,4-dimethylphospholes where R = H, Me, Ph, CN, OH, OMe, F, Cl, and Br. The aromaticity of the phospholyl rings is interpreted as a function of geometric, magnetic, and energetic indexes. It is shown, in agreement with previous experimental results, that phosphole aromaticity does not correlate with pyramidality at phosphorus. Variation of hyperconjugative and to a lesser extent, conjugative effects is responsible for the change in cyclic delocalization for the phospholes studied here.

AB - Quantum-chemical DFT calculations using the B3LYP functionals have been carried out for 1-R-substitued phospholes and some 1-R-substitued 3,4-dimethylphospholes where R = H, Me, Ph, CN, OH, OMe, F, Cl, and Br. The aromaticity of the phospholyl rings is interpreted as a function of geometric, magnetic, and energetic indexes. It is shown, in agreement with previous experimental results, that phosphole aromaticity does not correlate with pyramidality at phosphorus. Variation of hyperconjugative and to a lesser extent, conjugative effects is responsible for the change in cyclic delocalization for the phospholes studied here.

UR - https://www.scopus.com/pages/publications/0037154815

U2 - 10.1021/jo0108156

DO - 10.1021/jo0108156

M3 - Article

C2 - 11846664

AN - SCOPUS:0037154815

SN - 0022-3263

VL - 67

SP - 1208

EP - 1213

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 4

ER -

De-aromatizing phosphole

Abstract

Access to Document

Other files and links

Fingerprint

Cite this