The π Donating Ability of Heteroatoms

Fernando Bernardi; Angelo Mangini; Nicolaos D. Epiotis; J. R. Larson; Sason Shaik

doi:10.1021/ja00465a012

The π Donating Ability of Heteroatoms

Fernando Bernardi
, Angelo Mangini
, Nicolaos D. Epiotis
, J. R. Larson
, Sason Shaik

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

85 Scopus citations

Abstract

The π donating ability of heteroatoms in diverse systems such as⁺CH₂X, C₆H₅X, CH₂⩵CHX, and CH≡CX has been studied by means of SCFMO ab initio computations at the STO-3G and 4-31G levels. The results indicate that the π donating ability of first-row heteroatoms is larger than that of the second-row heteroatoms in systems where the adjacent fragment has a high-lying LUMO. On the other hand, the trend reverses when the adjacent fragment has a low-lying LUMO. A qualitative MO rationalization of these trends is offered and experimental evidence in support of the qualitative arguments is discussed.

Original language	English
Pages (from-to)	7465-7470
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	99
Issue number	23
DOIs	https://doi.org/10.1021/ja00465a012
State	Published - 1977
Externally published	Yes

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title = "The π Donating Ability of Heteroatoms",

abstract = "The π donating ability of heteroatoms in diverse systems such as+CH2X, C6H5X, CH2⩵CHX, and CH≡CX has been studied by means of SCFMO ab initio computations at the STO-3G and 4-31G levels. The results indicate that the π donating ability of first-row heteroatoms is larger than that of the second-row heteroatoms in systems where the adjacent fragment has a high-lying LUMO. On the other hand, the trend reverses when the adjacent fragment has a low-lying LUMO. A qualitative MO rationalization of these trends is offered and experimental evidence in support of the qualitative arguments is discussed.",

author = "Fernando Bernardi and Angelo Mangini and Epiotis, \{Nicolaos D.\} and Larson, \{J. R.\} and Sason Shaik",

year = "1977",

doi = "10.1021/ja00465a012",

language = "אנגלית",

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pages = "7465--7470",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

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TY - JOUR

T1 - The π Donating Ability of Heteroatoms

AU - Bernardi, Fernando

AU - Mangini, Angelo

AU - Epiotis, Nicolaos D.

AU - Larson, J. R.

AU - Shaik, Sason

PY - 1977

Y1 - 1977

N2 - The π donating ability of heteroatoms in diverse systems such as+CH2X, C6H5X, CH2⩵CHX, and CH≡CX has been studied by means of SCFMO ab initio computations at the STO-3G and 4-31G levels. The results indicate that the π donating ability of first-row heteroatoms is larger than that of the second-row heteroatoms in systems where the adjacent fragment has a high-lying LUMO. On the other hand, the trend reverses when the adjacent fragment has a low-lying LUMO. A qualitative MO rationalization of these trends is offered and experimental evidence in support of the qualitative arguments is discussed.

AB - The π donating ability of heteroatoms in diverse systems such as+CH2X, C6H5X, CH2⩵CHX, and CH≡CX has been studied by means of SCFMO ab initio computations at the STO-3G and 4-31G levels. The results indicate that the π donating ability of first-row heteroatoms is larger than that of the second-row heteroatoms in systems where the adjacent fragment has a high-lying LUMO. On the other hand, the trend reverses when the adjacent fragment has a low-lying LUMO. A qualitative MO rationalization of these trends is offered and experimental evidence in support of the qualitative arguments is discussed.

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 23

ER -

The π Donating Ability of Heteroatoms

Abstract

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