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.
UR - http://www.scopus.com/inward/record.url?scp=33847088756&partnerID=8YFLogxK
U2 - 10.1021/ja00465a012
DO - 10.1021/ja00465a012
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AN - SCOPUS:33847088756
SN - 0002-7863
VL - 99
SP - 7465
EP - 7470
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 23
ER -