Summary
N,N-Dialkylhydrazones [DAHs; R1R2C=1N-2N(R3)2] were prepared and their Kováts retention indices determined on 100% dimethylpolysiloxane (HP-1) and 5% diphenyl and 95% dimethylpolysiloxane (HP-5) stationary phases. The physico-chemical and retention behaviour of the DAHs depend greatly on whether R2=H or an alkyl group. A similar difference is observed in the alkane and oxo homomorphic factors of DAHs formed from aldehydes or ketones. The difference is explained on the basis of NMR and quantum-chemical results by intramolecular interactions between R2 and the lone pair of the2N atom. A single linear equation is suitable for prediction of retention indices if parameters are introduced representing resonance structure (bond angle and electron density) besidesI oxo or the van der Waals' surface.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
E. Fedelli, M. Cirimele, J. Chromatogr.15, 435 (1964).
Y. Hoshika, Y. Takata, J. Chromatogr.120, 379 (1976).
H. Van Langenhove, M. Van Acker, N. M. Schamp, Analyst108, 329 (1983).
É. János, J. Balla, E. Tyihák, R. Gáborjányi, J. Chromatogr.191, 239 (1980).
A. B. Attygalle, A. Zlatkis, H. S. Middledtich, J. Chromatogr.472, 284 (1989).
R. B. Mitra, G. B. Reddy, Syntheses, 694 (1989).
C. A. McDaniel, R. W. Howard, J. Chem. Acol.11, 303 (1985).
J. Rigaudy, S. P. Klesney (Editors), Nomenclature of Organic Chemistry, IUPAC Organic Chemistry Division, Pergamon Press, Oxford, 1976, p. 476.
G. J. Karabatsos, J. A. Taller, Tetrahedron24, 3923 (1968).
E. Kováts, Helv. Chim. Acta41, 1915 (1958).
M. Görgényi, H. Van Langenhove, Z. Király, J. Chromatogr.693, 181 (1995).
G. S. Goldin, S. N. Ciomo, G. S. Sor, Zh. Org. Khim.6, 754 (1970).
R. H. Wiley, S. C. Slaymaker, H. Kraus, J. Org. Chem.22, 201 (1957).
D. M. Lemal, F. Menger, E. Coats, J. Am. Chem. Soc.86, 2395 (1964).
M. Görgényi, L. Seres, J. C. S. Faraday Trans.87, 1827 (1991).
M. Görgényi, Z. Fekete, L. Seres, Chromatographia27, 581 (1989).
L. F. Clarke, F. O'Sullivan, A. F. Hagarty, J. C. S. Perkin Trans.2, 1649 (1991).
A. M. Matukuma, in “Gas Chromatography 1968” Ed. C. O. A. Harburn, Inst. Petroleum, London, 1969, pp. 55–72.
M. J. S. Dewar, W. Thiel, J. Am. Chem. Soc.99, 4899 (1977).
Gy. Tasi, I. Pálinko, J. Halász, G. Náray-Szabó, Semiempirical Quantum Chemical Calculations on Microcomputers, PcMol/486 Version 3.11; CheMicro Ltd, Budapest, 1992.
J. J. P. Stewart, MOPAC 6.1, QCPE program 455, 1991.
T. Körtvélyesi, M. Görgényi, L. Seres, Chromatographia41, 282 (1995).
P. W. Atkins, Physical Chemistry, Oxford University Press, 1994.
H. Lamparczyk, A. Radecki, Chromatographia18, 615 (1984).
R. C. Weast, (Editor), Handbook of Chemistry and Physics, CRC Press, Boca Raton, FL, 60th Ed. 1979.
J. P. Gouesnard, G. J. Martin, Org. Magn. Reson.12, 263 (1979).
A. Bondi, J. Phys. Chem.68, 441 (1964).
E. Hirsch, Anal. Chem.42, 1326 (1970).
F. Saura Calixto, A. Garcia Raso, Chromatographia14, 596 (1981).
G. Schomburg, J. Chromatogr.14, 157 (1964).
L. Soják, J. Krupcik, K. Tresarik, J. Janák, J. Chromatogr.65, 93 (1972).
T. F. Woloszyn, P. Jurs, Anal. Chem.65, 582 (1993).
E. Kováts, Adv. Chromatogr.46, 2708 (1963).
R. H. Rohrbaugh, P. C. Jurs, Anal. Chem.57, 2770 (1985).
K. Héberger, Chromatographia25, 725 (1988).
G. Schomburg, J. Chromatogr.23, 1 (1966).
G. Schomburg, J. Chromatogr.23 18 (1966).
L. Sojak, J. Hrivnák, P. Majer, J. Janák, Anal. Chem.45, 293 (1973).
G. Schomburg, G. Dielmann, J. Chromatogr. Sci.11, 151 (1973).
R. Ter Heide, J. Chromatogr.129, 143 (1976).
G. Anders, K. Anders, W. Engewald, Chromatographia20, 83 (1985).
J. Oszczapowicz, J. Osek, E. Dolecka, J. Chromatogr.315, 95 (1984).
J. Oszczapowicz, K. Ciszkowski, J. Osek, J. Chromatogr.362, 383 (1986).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Király, Z., Körtvélyesi, T., Seres, L. et al. Structure-retention relationships in the gas chromatography of N,N-dialkylhydrazones. Chromatographia 42, 653–659 (1996). https://doi.org/10.1007/BF02267697
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/BF02267697