TRANS-1,2-CYCLOHEXANEDICARBOXYLIC ACID-DERIVATIVES AS PH-TRIGGER FOR CONFORMATIONALLY CONTROLLED CROWNS

Authors
SAMOSHIN VV CHERTKOV VA VATLINA LP DOBRETSOVA EK SIMONOV NA KASTORSKY LP GREMYACHINSKY DE SCHNEIDER HJ
Citation
Vv. Samoshin et al., TRANS-1,2-CYCLOHEXANEDICARBOXYLIC ACID-DERIVATIVES AS PH-TRIGGER FOR CONFORMATIONALLY CONTROLLED CROWNS, Tetrahedron letters, 37(23), 1996, pp. 3981-3984
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
23
Year of publication
1996
Pages
3981 - 3984
Database
ISI
SICI code
0040-4039(1996)37:23<3981:TAAPFC>2.0.ZU;2-5
Abstract
Conversion of trans-1,2-cyclohexanedicarboxylic acid derivatives into dianions under the action of strong bases leads to dramatic conformati onal changes: a conformer with diaxial position of carboxylate groups becomes predominant. Thus the trans-1,2-cyclohexanedicarboxylic acid m oiety can be used for pH-induced conformational switching. The conform ational energy changes upon protonation amount to 10 kJ/mol. (C) 1996 Elsevier Science Ltd