Radical stabilizing ability of the ferrocenyl and cyclobutadieneiron tricarbonyl groups

被引:18
作者
Creary, X [1 ]
机构
[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA
关键词
D O I
10.1021/ol000119c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
GRAPHICS Computational studies indicate that ferrocenyl substituted methyl radicals owe their stability to a spin delocalization mechanism involving Fe and a major contribution from an eta(4) form, Cyclobutadieneiron tricarbonyl substituted methyl radicals are also calculated to be highly stabilized by spin delocalization onto Fe and a major contribution from an eta(3) form.
引用
收藏
页码:2069 / 2072
页数:4
相关论文
共 13 条
[1]  
Adam W, 1998, ADV PHOTOCH, V24, P205
[2]   Electronic effects of para- and meta-substituents on the EPR D parameter in 1,3-arylcyclopentane-1,3-diyl triplet diradicals. A new spectroscopic measure of alpha spin densities and radical stabilization energies in benzyl-type monoradicals [J].
Adam, W ;
Harrer, HM ;
Kita, F ;
Korth, HG ;
Nau, WM .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1419-1426
[3]   A COMPARISON OF THE RADICAL-STABILIZING ABILITY OF AROMATIC-GROUPS - GAMMA-VALUES FOR AROMATIC-GROUPS [J].
CREARY, X ;
MEHRSHEIKHMOHAMMADI, ME ;
MCDONALD, S .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12) :2904-2910
[4]   Methylenecyclopropane rearrangement as a probe for free radical substituent effects.: σ• values for potent radical-stabilizing nitrogen-containing substituents [J].
Creary, X ;
Engel, PS ;
Kavaluskas, N ;
Pan, L ;
Wolf, A .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5634-5643
[5]   STRUCTURE OF ALPHA-CYCLOBUTADIENYLIRON TRICARBONYL CARBONIUM IONS [J].
DAVIS, RE ;
SIMPSON, HD ;
GRICE, N ;
PETTIT, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (24) :6688-&
[6]   C13 NUCLEAR MAGNETIC-RESONANCE STUDY OF CYCLOBUTADIENEIRON TRICARBONYL-SUBSTITUTED CARBONIUM-IONS [J].
ESCHBACH, CS ;
SEYFERTH, D ;
REEVES, PC .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1976, 104 (03) :363-372
[7]  
Frisch M.J., 2016, Gaussian 16 Revision C. 01. 2016, V16, P01
[8]   An instance of trivalent carbon triphenylmethyl [J].
Gomberg, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1900, 22 (11) :757-771
[9]   A NEW TYPE OF ORGANO-IRON COMPOUND [J].
KEALY, TJ ;
PAUSON, PL .
NATURE, 1951, 168 (4285) :1039-1040
[10]   The molecular structure of ferrocene [J].
Koch, H ;
Jorgensen, P ;
Helgaker, T .
JOURNAL OF CHEMICAL PHYSICS, 1996, 104 (23) :9528-9530