Abstract
Lithocholic acid N-(2-aminoethyl)amide (1) and deoxycholic acid N-(2-aminoethyl)amide(2) have been prepared and characterized by1H, 13C and 15N NMR. The accurate molecular masses of 1 and 2 have been determined by ESI MS. The formation of the Cd2+-complexes (1+Cd and 2+Cd) in CD3OD solution have been detected by 1H,13C, 15N and 113Cd NMR. The 13C NMR chemical shift assignments of 1 and 2 and their Cd2+-complexes are based on DEPT-135 and z-GS 1H,13C HMQC experiments as well as comparison with the assignments of the related structures. The 15N NMR chemical shiftassignments of the ligands and theirCd2+-complexes are based on z-GS1H,15N HMBC experiments. 13C NMR chemical shift differences between 1and its 1:1 Cd2+-complex based on ab initiocalculations at Hartree-Fock SCI-PCM level using3-21G(d) basis set are in agreement with theexperimental shift changes observed onCd2+-complexation.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
A. P. Davis: Chem. Soc. Rev. 22, 243 (1993).
A. P. Davis, R. P. Bonar-Law, and J. K. M. Sanders: 'Receptors based on cholic acid', in Y. Murakami (ed.), Comprehensive Supramolecular Chemistry, Vol. 4, Elsevier Science Ltd., Oxford, 1996, pp. 257-286; (b) M. Miyata and K. Sada: 'Deoxycholic acid and related hosts', in D. D. MacNicol, F., and R. Bishop (eds.), Comprehensive Supramolecular Chemistry, Vol. 6, Elsevier Science Ltd., Oxford, 1996, pp. 147-176.
S. Broderick, A. P. Davis, and R. P. Williams: Tetrahedron Lett. 39, 6083 (1998) and references cited therein.
P. P. Nair and D. Kritchevsky: 'Chemistry of the bile acids', in P. P. Nair and D. Kritchevsky (eds.), The Bile Acids: Chemistry, Physiology and Metabolism, Vol. 1, Chemistry, Plenum Press, London, 1971, p. 8.
P. Granger: in P. S. Pregosin (ed.), Groups 11 and 12, Copper toMercury in Studies in Inorganic Chemistry, Transition Metal Nuclear Magnetic Resonance, Elsevier, Amsterdam, 1991, p. 293.
E. Kolehmainen, J. Tamminen, R. Kauppinen, and J. Linnanto: J. Incl. Phenom. Mol. Recogn. Chem. 35, 75-84 (1999).
P. S. Pandey and R. B. Singh: Tetrahedron Lett. 38, 5045 (1997).
Arthur Vogel: Elementary Practical Organic Chemistry, Part I, Preparations, Third edition revised by B. V. Smith and N. M. Waldron, Longman, London and New York, 1980, p. 225.
(a) K. Lappalainen: Ph.D. Thesis, Research Report No. 62, University of Jyväskylä, Department of Chemistry, Finland (1997) and references cited therein; (b) E. Kolehmainen, J. Tamminen, K. Lappalainen, T. Torkkel, and R. Seppälä: Synthesis, 1082 (1996); (c) K. Lappalainen, E. Kolehmainen and J. Kotoneva: Magn. Reson. Chem. 34, 316 (1996).
A. Bax, R. H. Griffey, and B. L. Hawkins: J. Magn. Reson. 55, 301 (1983).
A. Bax and S. Subramanian: J. Magn. Reson. 67, 565 (1986).
A. Bax and M. F. Summers: J. Am. Chem. Soc. 108, 2093 (1986).
M. Moini, B. L. Jones, R., M. Rogers and L. Jiang: J. Am. Mass. Spectrom. 9, 977 (1998).
J. J. P. Stewart: J. Comp. Chem. 10, 209 (1989).
SPARTAN, Version 5.0.2 (Wavefunction Inc., Irvine, CA, 1991-7).
M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, and J. A. Pople: GAUSSIAN 94, Revision B.1, Gaussian Inc., Pittsburgh PA (1995).
A. F. Hofmann and D. M. Small: Ann. Rev. Med. 18, 333 (1967).
M. Munakata, S. Kitagawa, and F. Yagi: Inorg. Chem. 25, 964 (1986).
S. Berger, S. Braun, and H.-O. Kalinowski: NMR Spectroscopy of the Non-Metallic Elements, John Wiley & Sons, Chichester, 1997, p. 231.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Tamminen, J., Kolehmainen, E., Linnanto, J. et al. 13C, 15N and 113Cd NMR and Molecular Orbital Studies of Novel Bile Acid N-(2-aminoethyl)amides and Their Cd2+-complexes. Journal of Inclusion Phenomena 37, 121–130 (2000). https://doi.org/10.1023/A:1008153126545
Issue Date:
DOI: https://doi.org/10.1023/A:1008153126545