ATTRACTIVE INTERACTIONS BETWEEN AN ALKYNE GROUP AND 2 CARBONYL OXYGEN-ATOMS - THE CRYSTAL-STRUCTURE AND MOLECULAR-STRUCTURE OF 2,2'-ETHYNYLENEDIBENZOIC ACID AT 150-K

被引:9
作者
PILKINGTON, M [1 ]
TAYYIP, S [1 ]
WALLIS, JD [1 ]
机构
[1] UNIV KENT,CHEM LAB,CANTERBURY CT2 7NH,KENT,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1994年 / 12期
关键词
D O I
10.1039/p29940002481
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The X-ray crystal structure of 8 shows two attractive intramolecular interactions between sp carbon atoms and adjacent carbonyl oxygen atoms, leading to a twisting of the triple bond equivalent to an orthogonal combination of cis and trans bends; the two carboxylic acid groups lie to the same side of the triple bond to avoid unfavourable contacts between carbonyl oxygen atoms and incipient carbanionic centres.
引用
收藏
页码:2481 / 2484
页数:4
相关论文
共 25 条
[1]   INTERNAL-ROTATION IN TOLANE - MOLECULAR-STRUCTURE IN GAS AND CRYSTAL PHASES [J].
ABRAMENKOV, AV ;
ALMENNINGEN, A ;
CYVIN, BN ;
CYVIN, SJ ;
JONVIK, T ;
KHAIKIN, LS ;
ROMMING, C ;
VILKOV, LV .
ACTA CHEMICA SCANDINAVICA SERIES A-PHYSICAL AND INORGANIC CHEMISTRY, 1988, 42 (10) :674-684
[2]   ADDITION-REACTIONS OF HETEROCYCLIC-COMPOUNDS .74. PRODUCTS FROM DIMETHYL ACETYLENEDICARBOXYLATE WITH THIOUREA, THIOAMIDE, AND GUANIDINE DERIVATIVES [J].
ACHESON, RM ;
WALLIS, JD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (02) :415-422
[3]  
BAXTER PNW, 1993, J CHEM SOC CHEM COMM, P1135
[4]   VAN DER WAALS VOLUMES + RADII [J].
BONDI, A .
JOURNAL OF PHYSICAL CHEMISTRY, 1964, 68 (03) :441-+
[5]   SOME REACTIONS OF TETRAKIS (TERT-BUTYLIMIDO) OSMIUM (VIII) - X-RAY CRYSTAL-STRUCTURES OF OS(NBUT)O(O2CBUT)2(NH2BUT)2.BUTCO2H, (BUTN)2OS(MU-NBUT)2OS(NBUT)X2 (X = CL OR I) AND [OS2(NBUT)4(MU-NBUT)2]I3 [J].
DANOPOULOS, AA ;
WILKINSON, G ;
HUSSAINBATES, B ;
HURSTHOUSE, MB .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1991, (08) :1855-1860
[6]   STUDY OF VINYL ANION SYSTEM - REARRANGEMENTS AND FORMATION FROM H- AND ACETYLENE [J].
DYKSTRA, CE ;
ARDUENGO, AJ ;
FUKUNAGA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (19) :6007-6012
[7]   NUCLEOPHILIC-ADDITION TO A TRIPLE BOND - PRELIMINARY ABINITIO STUDY [J].
EISENSTEIN, O ;
PROCTER, G ;
DUNITZ, JD .
HELVETICA CHIMICA ACTA, 1978, 61 (07) :2538-2541
[8]   SYN AND ANTI TRANSITION-STATES IN THE ADDITION OF AMMONIA TO CYANOACETYLENE - FORMATION OF A STABLE ZWITTERIONIC INTERMEDIATE [J].
HOUK, KN ;
STROZIER, RW ;
ROZEBOOM, MD ;
NAGASE, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (01) :323-325
[9]   METHYL 2-[(2,6-DIMETHOXYPHENYL)ETHYNYL]BENZOATE [J].
HUANG, ET ;
EVANS, KL ;
FRONCZEK, FR ;
GANDOUR, RD .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1991, 47 :2727-2729
[10]  
HUDSON RF, 1994, HETEROCYCLES, V37, P1933