Cation-anion CH•••O- interactions in the metal-free phenolate, tetra-n-butylammonium phenol-phenolate

被引：40

作者：

Goddard, R ^{[1
]}

Herzog, HM ^{[1
]}

Reetz, MT ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

来源：

TETRAHEDRON | 2002年 / 58卷 / 39期

关键词：

tetra-n-butylammonium phenol-phenolate; ion pair interaction; metal-free phenolate;

D O I：

10.1016/S0040-4020(02)00900-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Deprotonation of phenol by tetra-n-butylammonium hydroxide and subsequent removal of water by P2O5 results in quantitative formation of tetra-n-butylammonium phenol-phenolate. The compound crystallizes as an ion pair, with the solute phenol molecule intimately attached to the phenolate anion by an O-H...O- hydrogen bond (O...O 2.471(5) Angstrom). A short contact between one alpha-C atom of the tetra-n-butylammonium cation and the phenolate O atom indicates that the ion pair interaction is strengthened by an additional C-H...O- hydrogen-bond, despite the attached phenol. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：7847 / 7850

页数：4

共 46 条

[1] Asymmetric Weitz-Scheffer epoxidation of isoflavones with hydroperoxides mediated by optically active phase-transfer catalysts [J].

Adam, W ;

Rao, PB ;

Degen, HG ;

Levai, A ;

Patonay, T ;

Saha-Möller, CR .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) :259-264

[2] AN INVESTIGATION OF THE EFFECTS OF THE MEDIUM AND THE TYPE OF FLUORIDE ON THE HYDROGEN-BOND ASSISTED ALKYLATION OF PHENOLS [J].

ALAUDDIN, MM ;

MILLER, JM ;

CLARK, JH .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (02) :263-265

[3] Enantiomerically enriched (R)- and (S)-α-methylphenylalanine via asymmetric PTC C-alkylation catalysed by NOBIN [J].

Belokon', YN ;

Kochetkov, KA ;

Churkina, TD ;

Ikonnikov, NS ;

Vyskocil, S ;

Kagan, HB .

TETRAHEDRON-ASYMMETRY, 1999, 10 (09) :1723-1728

[4] Oxidation of diorganopalladium(II) complexes by water and halogens: Reactions involving methyl group transfer and structural studies of hydrogen-bonded adducts formed by aryl alcohols with the pallada(IV)cyclopentane complex Pd(CH2CH2CH2CH2)(OH){(pz)(3)BH}([(pz)(3)BH](-)=tris(pyrazol-1-yl)borate) [J].

Canty, AJ ;

Jin, H ;

Roberts, AS ;

Skelton, BW ;

White, AH .

ORGANOMETALLICS, 1996, 15 (26) :5713-5722

[5] TRIANGULAR PHENOXIDE AGGREGATES OF CALCIUM, STRONTIUM, AND BARIUM - A COMPARISON [J].

CAULTON, KG ;

CHISHOLM, MH ;

DRAKE, SR ;

FOLTING, K ;

HUFFMAN, JC ;

STREIB, WE .

INORGANIC CHEMISTRY, 1993, 32 (10) :1970-1976

[6] Enantioselective Michael addition of nitromethane to α,β-enones catalyzed by chiral quaternary ammonium salts.: A simple synthesis of (R)-baclofen [J].

Corey, EJ ;

Zhang, FY .

ORGANIC LETTERS, 2000, 2 (26) :4257-4259

[7] A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions [J].

Corey, EJ ;

Xu, F ;

Noe, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12414-12415

[8]

Cowan J.A., 2002, ANGEW CHEM, V114, P1490, DOI DOI 10.1002/1521-3757(20020415)114:8<1490::AID-ANGE1490>3.0.CO

[9]

2-6

[10]

Cowan JA, 2002, ANGEW CHEM INT EDIT, V41, P1432, DOI 10.1002/1521-3773(20020415)41:8<1432::AID-ANIE1432>3.0.CO

← 1 2 3 4 5 →