A computational study of proton and electron affinities

被引：26

作者：

Sauers, RR ^{[1
]}

机构：

[1] Rutgers State Univ, Dept Chem, New Brunswick, NJ 08903 USA

来源：

TETRAHEDRON | 1999年 / 55卷 / 33期

关键词：

carbanions; radicals and radical reactions; theoretical studies; hydrocarbons;

D O I：

10.1016/S0040-4020(99)00560-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Proton and electron affinities were calculated for a series of 28 carbanions and radicals using MP2/6-31 and B3LYP methods. Structural and electronic factors that control anion and radical stabilization were examined by natural bond orbital analyses. New examples of hyperconjugation were found for lone pairs and radical centers and adjacent C-H* and C-C* orbitals. Correlations between %-s-character of C-H bonds and anions with proton affinity were poor. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：10013 / 10026

页数：14

共 50 条

[41] Ring opening of the cyclopropylcarbinyl radical and its N- and O-substituted analogues.: A theoretical examination of very fast unimolecular reactions
Smith, DM
Nicolaides, A
Golding, BT
Radom, L
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (39) : 10223 - 10233
[42] ALLYLCARBINYL-CYCLOPROPYLCARBINYL NORBORNENYL-NORTRICYCLYL ANION REARRANGEMENT - EVIDENCE FOR A SYMMETRICAL INTERMEDIATE
STILLE, JK
SANNES, KN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (24) : 8494 - &
[43] STREITWIESER A, 1980, COMPREHENSIVE CARBAN, pCH7
[44] Cost effective calculation of molecular charge distributions and gas phase deprotonation energies using density functional methods
VanLier, G
DeProft, F
Geerlings, P
[J]. CHEMICAL PHYSICS LETTERS, 1997, 274 (04) : 396 - 404
[45] BRIDGEHEAD RADICALS
WALTON, JC
[J]. CHEMICAL SOCIETY REVIEWS, 1992, 21 (02) : 105 - 112
[46] DETERMINATION OF THE STABILIZATION ENERGY OF THE CYCLOPROPYLMETHYL RADICAL BY ELECTRON-PARAMAGNETIC-RES SPECTROSCOPY
WALTON, JC
[J]. MAGNETIC RESONANCE IN CHEMISTRY, 1987, 25 (11) : 998 - 1000
[47] Redox properties of free radicals
Wayner, DDM
Houmam, A
[J]. ACTA CHEMICA SCANDINAVICA, 1998, 52 (04): : 377 - 384
[48] APPLICATION OF POPLE-SANTRY-SEGAL CNDO METHOD TO CYCLOPROPYLCARBINYL AND CYCLOBUTYL CATION AND TO BICYCLOBUTANE
WIBERG, KB
[J]. TETRAHEDRON, 1968, 24 (03) : 1083 - +
[49] Pyramidalized olefins: Ab initio study and X-ray structure determination of bicyclo[2.2.2]octadienes
Williams, RV
Edwards, WD
Gadgil, VR
Colvin, ME
Seidl, ET
van der Helm, D
Hossain, MB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (15) : 5268 - 5271
[50] NON-PLANARITY OF PI SYSTEMS - AN ABINITIO STUDY OF NORBORNENE AND NORBORNADIENE
WIPFF, G
MOROKUMA, K
[J]. TETRAHEDRON LETTERS, 1980, 21 (46) : 4445 - 4448

← 1 2 3 4 5 →