Study of the sulfur atom as hydrogen bond acceptor in N(2)-pyridylmethyl- N'-arylthioureas
Por:
Valdés-Martínez J., Hernández-Ortega S., Rubio M., Li D.T., Swearingen J.K., Kaminsky W., Kelman D.R., West D.X.
Publicada:
1 ene 2004
Resumen:
The hydrogen acceptor capability of the sulfur atom in the biologically relevant N-2-pyridylmethyl-N?-arilthioureas was explored. N-2-Pyridylmethyl thioreas were selected to avoid the formation of intramolecular six-membered hydrogen-bonded ring. The compounds studied were N-2-pyridylmethyl-N?-phenylthiourea (1), N-2-pyridylmethyl-N?-2- methoxythiourea (2), N-2-pyridylmethyl-N?-4-methoxyphenylthiourea (3), and N-2-pyridylmethyl-N?-4-bromophenylthiourea (4). 1 crystallizes in the monoclinic space group P2 1/c, with a = 7.419(1) Å, b = 18.437(2) Å, c = 9.656(1) Å, ? = 106.277(6)°, V = 1267.8(3) Å 3, Z = 4. 2 crystallizes in the monoclinic space group P2 1/c, with a = 8.064(2) Å, b = 18.382(7) Å, c = 9.865(5) Å, ? = 97.81(3)°, V = 1448.8(11) Å 3, Z = 4. 3 crystallizes in the monoclinic space group P2 1/c, with a = 11.472(1) Å, b = 13.520(1) Å, c = 10.088(1) Å, ? = 112.60(1)°, V = 1444.5(2) Å 3, Z = 4. 4 crystallizes in the triclinic space group P-1, with a = 4.583(3) Å, b = 10.263(3) Å, c = 14.396(3) Å, ? = 77.92(2)°, ? = 88.55(4)°, ? = 80.02(4)°, V = 652.1(5) Å 3, Z = 2. Both thiourea N-H groups form intermolecular hydrogen bonds, one with the thione sulfur atom and the other with the pyridine nitrogen atom but the H-bonding schemes are not the same maybe due to the flexibility of the molecules.
Filiaciones:
Valdés-Martínez J.:
Instituto de Química, Univ. Nac. Auton. de Mex., Circuito Exterior S/n, Cd. Univ., C., Mexico
Hernández-Ortega S.:
Instituto de Química, Univ. Nac. Auton. de Mex., Circuito Exterior S/n, Cd. Univ., C., Mexico
Rubio M.:
Instituto de Química, Univ. Nac. Auton. de Mex., Circuito Exterior S/n, Cd. Univ., C., Mexico
Li D.T.:
Department of Chemistry, Illinois State University, Normal, Illinois, United States
Swearingen J.K.:
Department of Chemistry, Illinois State University, Normal, Illinois, United States
Kaminsky W.:
Department of Chemistry 351700, University of Washington, Seattle, Washington, United States
Kelman D.R.:
Department of Chemistry 351700, University of Washington, Seattle, Washington, United States
West D.X.:
Department of Chemistry 351700, University of Washington, Seattle, Washington, United States
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