Nucleophilicity of the bis(4-nitrophenyl)methyl anion

被引：8

作者：

Berger, Stefan T. A. ^{[1
]}

Lemek, Tadeusz ^{[2
]}

Mayr, Herbert ^{[1
]}

机构：

[1] Univ Munich, Dept Chem & Biochem, Butenandtstr 5-13 Haus F, D-81377 Munich, Germany

[2] Agr Univ Krakow, Dept Chem, PL-31120 Krakow, Poland

来源：

ARKIVOC | 2008年

关键词：

Kinetics; linear free energy relationship; nucleophilicity; intrinsic barriers;

D O I：

10.3998/ark.5550190.0009.a05

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Kinetics of the reactions of the bis(4-nitrophenyl)methyl anion 1 with quinone methides and other Michael acceptors have been measured in dimethyl sulfoxide solution at 20 degrees C. The second-order rate constants k(2) have been used to determine the nucleophilicity parameters N = 19.9 and s = 0.67 of 1 according to the linear free energy relationship log k(20 degrees C) = s(N + E).

引用

页码：37 / 53

页数：17

共 50 条

[11] 4-methyl-N-(4-nitrophenyl) benzenesulfonamide
Xing, JD
Zeng, T
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2005, 61 : O4318 - O4319
[12] Methyl N-(4-nitrophenyl)carbamate
Cai, Qun
Fei, Zhuan
Li, Lin
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O1494 - U1389
[13] A density functional investigation of 1,3-bis(4-nitrophenyl)urea as anion receptor
Wanno, Banchob
Rakrai, Wandee
Keawwangchai, Somchai
Morakot, Neramit
Morakot, Nongnit
Nunthaboot, Nadtanet
Ruangpornvisuti, Vithaya
JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2009, 902 (1-3): : 33 - 40
[14] Methyl 2-[hydroxy(4-nitrophenyl)methyl]acrylate
Yin, CX
Huo, FJ
Yang, P
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2004, 60 : O1332 - O1333
[15] ELECTROORGANIC SYNTHESIS .3. NOVEL SYNTHESIS OF BIS(4-NITROPHENYL) SULFONE AND BIS(4-NITROPHENYL) SULFOXIDE BY ANODIC-OXIDATION
NISHIGUCHI, I
TAKUMI, H
TODA, M
HIRASHIMA, T
NIPPON KAGAKU KAISHI, 1984, (11) : 1838 - 1841
[16] Bis(4-nitrophenyl) N,N-dimethylphosphoramidate
Gholivand, K
Tadjarodi, A
Taeb, A
Garivani, G
Ng, SW
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2001, 57 : O472 - O473
[17] 1,3-bis(4-nitrophenyl)triazene
Hörner, M
Bresolin, L
Bordinhao, J
Hartmann, E
Strähle, J
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2003, 59 : O426 - O427
[18] N,N-Bis(4-nitrophenyl) acetamide
Nanaura, Kokichi
Okuno, Tsunehisa
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O457 - +
[19] N-{[(4-Nitrophenyl)amino]methyl}benzamide
Buzarevski, Antonio
Mikhova, Bozhana
Popovski, Emil
MOLBANK, 2014, (01)
[20] Synthesis of phenyl or 4-nitrophenyl methyl β-ketophosphonate esters
Reddy, PM
Viragh, C
Kovach, IM
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2002, 177 (6-7) : 1597 - 1600

← 1 2 3 4 5 →