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Volumn 217, Issue 5, 2002, Pages 217-222

Intramolecular hydrogen bond and proton transfer in 3-(2-benzimidazolylthio)-2,4-pentanedione. Crystallographic evidence and theoretical calculations

Author keywords

[No Author keywords available]

Indexed keywords

3 (2 BENZIMIDAZOLYLTHIO) 2,4 PENTANEDIONE; BENZIMIDAZOLE DERIVATIVE; MALONALDEHYDE; UNCLASSIFIED DRUG;

EID: 0036396118     PISSN: 00442968     EISSN: None     Source Type: Journal    
DOI: 10.1524/zkri.217.5.217.20633     Document Type: Article
Times cited : (3)

References (27)
  • 1
    • 0021409432 scopus 로고
    • Microwave spectroscopic study of malonaldehyde. 3. Vibration-rotation interaction and one-dimensional model from proton tunneling
    • Baughcum, S. L.; Smith, Z.; Wilson, E. B.; Duerst, R. W.: Microwave spectroscopic study of malonaldehyde. 3. Vibration-rotation interaction and one-dimensional model from proton tunneling. J. Am. Chem. Soc. 106 (1984) 2260-2265.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 2260-2265
    • Baughcum, S.L.1    Smith, Z.2    Wilson, E.B.3    Duerst, R.W.4
  • 2
    • 84977289324 scopus 로고
    • An empirical correction for absorption anisotropy
    • Blessing, R. H.: An empirical correction for absorption anisotropy. Acta Cryst. A51 (1995) 33-38.
    • (1995) Acta Cryst. , vol.A51 , pp. 33-38
    • Blessing, R.H.1
  • 3
    • 0004150157 scopus 로고    scopus 로고
    • Bruker Axs Inc., Madison, Wisconsin, USA. SHELXTL Version 6.10 (201).
    • SHELXTL Version 6.10 , pp. 201
  • 4
    • 0033515394 scopus 로고    scopus 로고
    • A new ONIOM implementation in Gaussian 98. Part I. The calculation of energies, gradients, vibrational frequencies and electric field derivatives
    • Dapprich, S.; I. Komáromi, I.; Byun, K. S.; Morokuma, K.; Frisch, M. J.: A new ONIOM implementation in Gaussian 98. Part I. The calculation of energies, gradients, vibrational frequencies and electric field derivatives. J. Mol. Struct. (Theochem) (1999) 461-462, 1-21.
    • (1999) J. Mol. Struct. (Theochem) , vol.461-462 , pp. 1-21
    • Dapprich, S.1    Komáromi, I.I.2    Byun, K.S.3    Morokuma, K.4    Frisch, M.J.5
  • 5
    • 0001478784 scopus 로고
    • The crystal and molecular structure of 5-amino-2-thiol-1,3,4-thiadiazole
    • Downie, T. C.; Harrison, W.; Raper, E. S.; Hepworth, M.A.: The crystal and molecular structure of 5-amino-2-thiol-1,3,4-thiadiazole. Acta Cryst. B28 (1972) 1584-1590.
    • (1972) Acta Cryst. , vol.B28 , pp. 1584-1590
    • Downie, T.C.1    Harrison, W.2    Raper, E.S.3    Hepworth, M.A.4
  • 6
    • 0001496983 scopus 로고
    • B-diketone interactions. Part 10. The structure and properties of 3-(2′,4′-dimethoxyphenyl) pentane-2,4-dione; enol ring symmetry and other hydrogen bond parameters
    • Emsley, J.; Lewina, Y. Y. Ma.; Karaulov, S. A; Motevalli, M.; Hursthouse, M. B.: B-diketone interactions. Part 10. The structure and properties of 3-(2′,4′-dimethoxyphenyl) pentane-2,4-dione; enol ring symmetry and other hydrogen bond parameters. Journal of Molecular Structure 216 (1990) 143-152.
    • (1990) Journal of Molecular Structure , vol.216 , pp. 143-152
    • Emsley, J.1    Lewina, Y.Y.Ma.2    Karaulov, S.A.3    Motevalli, M.4    Hursthouse, M.B.5
  • 7
    • 0000452218 scopus 로고
    • The crystal and molecular structure of 2-mercaptobenzimidazole
    • Form, G. R.; Raper, E. S.; Downie, T. C.: The crystal and molecular structure of 2-mercaptobenzimidazole. Acta Cryst. B32 (1976) 345-348.
    • (1976) Acta Cryst. , vol.B32 , pp. 345-348
    • Form, G.R.1    Raper, E.S.2    Downie, T.C.3
  • 8
    • 0010784032 scopus 로고
    • X-ray crystal analysis of the substrates of aconitase. X. The structure of dipotassium cis-aconitate
    • Glusker, J. P.; Orehovsky Jr., W.; Casciato, C. A.; Carell, H. L.: X-ray crystal analysis of the substrates of aconitase. X. The structure of dipotassium cis-aconitate. Acta Cryst. B28 (1972) 419-425.
    • (1972) Acta Cryst. , vol.B28 , pp. 419-425
    • Glusker, J.P.1    Orehovsky W., Jr.2    Casciato, C.A.3    Carell, H.L.4
  • 10
    • 10844256940 scopus 로고
    • Evidence for resonance-assisted hydrogen-bonding from crystal-structure correlations on the enol from of the β-diketone fragment
    • Gilli, G.; Bellucci, F.; Ferretti, V.; Bertolasi, V.: Evidence for resonance-assisted hydrogen-bonding from crystal-structure correlations on the enol from of the β-diketone fragment. J. Am. Soc. 111 (1989) 1023-1028.
    • (1989) J. Am. Soc. , vol.111 , pp. 1023-1028
    • Gilli, G.1    Bellucci, F.2    Ferretti, V.3    Bertolasi, V.4
  • 11
    • 0346213329 scopus 로고
    • Heterocyclic system containing bridgehead nitrogen atom: Part XXXIV. Reaction of 4-chloro-2-mercaptobenzimidazole with chloroacetic acid, β-bromopropionic acid, α-halogenoketone and 1,2-dibromoethane
    • Gupta, R. P.; Handa, R. N.; Pujari, H. K.: Heterocyclic System Containing Bridgehead Nitrogen Atom: Part XXXIV. Reaction of 4-Chloro-2-mercaptobenzimidazole with Chloroacetic Acid, β-Bromopropionic Acid, α-Halogenoketone and 1,2-Dibromoethane. Indian J. Chem., Sect. B (1979) 17B 572-574.
    • (1979) Indian J. Chem., Sect. B , vol.17 B , pp. 572-574
    • Gupta, R.P.1    Handa, R.N.2    Pujari, H.K.3
  • 13
    • 0010922564 scopus 로고
    • Heterocyclic system containing bridge-head nitrogen atom: Part XXXIX. Reaction of 2-mercapto-4-bromo-6-methylbenzimidazole with chloroacetic acid and 1,2-dibromoethane
    • Jain, K. K.; Pujari, H. K.: Heterocyclic System Containing Bridge-head Nitrogen Atom: Part XXXIX. Reaction of 2-Mercapto-4-bromo-6-methylbenzimidazole with Chloroacetic Acid and 1,2-Dibromoethane. Indian J. Chem., Sect. B (1981) 20B 294-295.
    • (1981) Indian J. Chem., Sect. B , vol.20 B , pp. 294-295
    • Jain, K.K.1    Pujari, H.K.2
  • 14
    • 0000452223 scopus 로고
    • The crystal and molecular structure of the enol form of 1-phenyl-1,3-butanedione (benzoylacetone) by neutron diffraction
    • Jones, R. D. G.: The crystal and molecular structure of the enol form of 1-phenyl-1,3-butanedione (benzoylacetone) by neutron diffraction. Acta Cryst. B32 (1976) 2133-2136.
    • (1976) Acta Cryst. , vol.B32 , pp. 2133-2136
    • Jones, R.D.G.1
  • 15
    • 0010861904 scopus 로고
    • Acetylation and cyclization reactions of some imidazole derivatives containing 1,3-dicarbonyl system
    • Koóš, M.: Acetylation and cyclization reactions of some imidazole derivatives containing 1,3-dicarbonyl system. Chem. Papers 48(2) (1994a) 108-110.
    • (1994) Chem. Papers , vol.48 , Issue.2 , pp. 108-110
    • Koóš, M.1
  • 16
    • 21844521996 scopus 로고
    • Synthesis and antimicrobial activity of some 2-Alkyl-2H-1,4-benzothiazin-3(4H)-ones and 2-Alkylbenzo[d]imidazolo[2,1-b]-thiazolidin-3-ones
    • Koóš, M.: Synthesis and Antimicrobial Activity of Some 2-Alkyl-2H-1,4-benzothiazin-3(4H)-ones and 2-Alkylbenzo[d]imidazolo[2,1-b]-thiazolidin-3-ones. Monatsh. Chem. (1994b) 125 1011-1016.
    • (1994) Monatsh. Chem. , vol.125 , pp. 1011-1016
    • Koóš, M.1
  • 17
    • 0002732736 scopus 로고
    • Influence of structure on antimicrobial activity of some heterocycles III. 1-substituted 2-methyl-5-nitroimidazoles
    • Koóš, M.; Novotná, Z.; Rybár, A.; Influence of Structure on Antimicrobial Activity of Some Heterocycles III. 1-Substituted 2-Methyl-5-nitroimidazoles. Chem. Papers (1994) 48 50-54.
    • (1994) Chem. Papers , vol.48 , pp. 50-54
    • Koóš, M.1    Novotná, Z.2    Rybár, A.3
  • 18
    • 4243878704 scopus 로고    scopus 로고
    • Hydrogen bond studies. CXLII. Neutron difffraction study of the two very short hydrogen bonds in lithium hydrogen phtalate-metanol
    • Küppers, H.; Kvick, Å.; Olovsson, I.: Hydrogen bond studies. CXLII. Neutron difffraction study of the two very short hydrogen bonds in lithium hydrogen phtalate-metanol. Acta Cryst. B37 (1981) 1203-1207.
    • Acta Cryst. B , vol.37 , Issue.1981 , pp. 1203-1207
    • Küppers, H.1    Kvick, Å.2    Olovsson, I.3
  • 19
    • 0010783520 scopus 로고
    • Commercial applications of benzimidazoles
    • Preston, P. N.: Commercial applications of benzimidazoles. Chem. Heterocycl. Compd. (1980) 40 531-542.
    • (1980) Chem. Heterocycl. Compd. , vol.40 , pp. 531-542
    • Preston, P.N.1
  • 21
    • 0000613983 scopus 로고
    • An ab initio study of the conformation and intramolecular proton transfer in the enol form of acetylacetone
    • Rios, M.A.; Rodrīguez, J.: An ab initio study of the conformation and intramolecular proton transfer in the enol form of acetylacetone. Journal of Molecular Structure (Theochem) 204 (1990) 137-144.
    • (1990) Journal of Molecular Structure (Theochem) , vol.204 , pp. 137-144
    • Rios, M.A.1    Rodriguez, J.2
  • 22
    • 26344435738 scopus 로고
    • Fully optimized contracted Gaussian basis sets for atoms Li to Kr
    • Schäfer A.; Horn, H.; Alhrichs, R.: Fully optimized contracted Gaussian basis sets for atoms Li to Kr. J. Chem. Phys 97 (1992) 2571-2577.
    • (1992) J. Chem. Phys. , vol.97 , pp. 2571-2577
    • Schäfer, A.1    Horn, H.2    Alhrichs, R.3
  • 23
    • 0004283944 scopus 로고    scopus 로고
    • University of Göttingen, Germany
    • Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany.
    • (2001) SADABS
    • Sheldrick, G.M.1
  • 24
    • 0010861155 scopus 로고    scopus 로고
    • Analytical X-ray Instruments Inc., Madison, Wisconsin, USA
    • Siemens (2001). SMART, SAINT and XPREP. Siemens Analytical X- ray Instruments Inc., Madison, Wisconsin, USA.
    • (2001) SMART, SAINT and XPREP. Siemens
  • 25
    • 0033481426 scopus 로고    scopus 로고
    • Infrared absorption and Raman scattering of (Z)-3-hydroxypropenal. A density functional theoretical study
    • Spangert-Larsen, J.: Infrared absorption and Raman scattering of (Z)-3-hydroxypropenal. A density functional theoretical study. Chemical Physics 240 (1999) 51-61.
    • (1999) Chemical Physics , vol.240 , pp. 51-61
    • Spangert-Larsen, J.1
  • 27
    • 33748617338 scopus 로고    scopus 로고
    • A single crystal neutron diffraction study of the temperature dependence of hydrogen-atom disorder in benzoic acid dimers
    • Wilson, C. C.; Shankland, N.; Florence, A. J.: A single crystal neutron diffraction study of the temperature dependence of hydrogen-atom disorder in benzoic acid dimers. J. Chem. Soc., Faraday Trans. 92(24) (1996) 5051-5057.
    • (1996) J. Chem. Soc., Faraday Trans. , vol.92 , Issue.24 , pp. 5051-5057
    • Wilson, C.C.1    Shankland, N.2    Florence, A.J.3


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