Intramolecular hydrogen bonds in N-oxides of Schiff bases

被引:5
|
作者
Dziembowska, T
Majewski, E
Rozwadowski, Z
Brzezinski, B
机构
[1] ADAM MICKIEWICZ UNIV POZNAN,FAC CHEM,PL-60780 POZNAN,POLAND
[2] TECH UNIV SZCZECIN,INST FUNDAMENTAL CHEM,PL-71065 SZCZECIN,POLAND
关键词
N-oxide of Schiff base; intramolecular hydrogen bond; proton transfer; H-1 and C-13 NMR; FTIR spectroscopy;
D O I
10.1016/S0022-2860(96)09414-8
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Three N-oxides of Schiff bases (nitrones) with intramolecular hydrogen bonds were synthesized and studied by FTIR as well as H-1 and C-13 NMR methods. In the -O-H ... ON reversible arrow =O ... H-ON intramolecular hydrogen bonds the protons fluctuate, whereas the weight of the =O ... H-ON structure is low. In the FTIR spectra of these compounds very weak continua were found and explained by an electronically conjugation between donor and acceptor groups in the intramolecular hydrogen bond. Such bonds show almost no Zundel polarizability. (C) 1997 Elsevier Science B.V.
引用
收藏
页码:183 / 187
页数:5
相关论文
共 50 条
  • [41] INTRAMOLECULAR HYDROGEN BONDS .X. INTRAMOLECULAR HYDROGEN BONDING IN OMEGA-N N-DIETHYLAMINOALKANOLS
    MORI, N
    NAKAMURA, E
    TSUZUKI, Y
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1967, 40 (09) : 2191 - +
  • [42] Stabilization of fulleropyrrolidine N-oxides through intrarotaxane hydrogen bonding
    Mateo-Alonso, Aurelio
    Brough, Peter
    Prato, Maurizio
    CHEMICAL COMMUNICATIONS, 2007, (14) : 1412 - 1414
  • [43] SNH reactions of 1,2,4-triazine N-oxides, pyrazine N-oxides, and pterin N-oxides with arenethiols
    Kozhevnikov, DN
    Kovalev, IS
    Rusinov, VL
    Chapakhin, ON
    RUSSIAN CHEMICAL BULLETIN, 2001, 50 (06) : 1068 - 1071
  • [44] α-Benzotriazolylpyridines and their N-oxides
    Katritzky, AR
    Kurz, T
    Zhang, SM
    Voronkov, M
    HETEROCYCLES, 2001, 55 (09) : 1703 - +
  • [45] The intramolecular hydrogen bonds in some Schiff bases derived from dendrimers: DAB-Am-8 and PAMAM-G2
    Schilf, W.
    Kolodziej, B.
    Grech, E.
    JOURNAL OF MOLECULAR STRUCTURE, 2006, 791 (1-3) : 93 - 97
  • [46] SNH reactions of 1,2,4-triazine N-oxides, pyrazine N-oxides, and pterin N-oxides with arenethiols*
    D. N. Kozhevnikov
    I. S. Kovalev
    V. L. Rusinov
    O. N. Chupakhin
    Russian Chemical Bulletin, 2001, 50 : 1068 - 1071
  • [47] POTENTIOMETRIC INVESTIGATIONS OF INTRAMOLECULAR 9-MEMBERED AND 10-MEMBERED RING HYDROGEN-BONDS OBSERVED IN SCHIFF-BASES
    GUNDUZ, T
    GUNDUZ, N
    KILIC, E
    ATAKOL, O
    KOSEOGLU, F
    ANALYTICA CHIMICA ACTA, 1991, 249 (02) : 427 - 431
  • [48] HYDROGEN-BONDING BETWEEN PYRIDINE N-OXIDES AND NITROPHENOLS
    BUENO, WA
    BLAZ, NA
    SANTOS, MJM
    ANAIS DA ACADEMIA BRASILEIRA DE CIENCIAS, 1984, 56 (01): : 63 - 69
  • [49] AZOLOQUINOXALINE N-OXIDES
    CUE, BW
    CZUBA, LJ
    DIRLAM, JP
    JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (21): : 4125 - 4128
  • [50] N-OXIDES OF AZAANTHRAQUINONES
    OCANA, B
    ESPADA, M
    AVENDANO, C
    TETRAHEDRON, 1994, 50 (31) : 9505 - 9510