Structural studies of N-2-(3-picolyl)- and N-2-(4-picolyl)-N' -tolylthioureas
Por:
Valdés-Martínez J., Hernández-Ortega S., Hermetet A.K., Ackerman L.J., Presto C.A., Swearingen J.K., Kelman D.R., Goldberg K.I., Kaminsky W., West D.X.
Publicada:
1 ene 2002
Resumen:
Reactions of 2-aminopicolines with 2- and 4-tolyl isothiocyanates yielded N-2-(4-picolyl)-N?-4-tolylthiourea, 1, N-2-(3-picolyl)-N? -4-tolylthiourea, 2, and N-2-(4-picolyl)-N?-2-tolylthiourea, 3. Compound 1 is monoclinic, of space group P21/c with a = 7.456(1) Å, b = 13.135(3) Å, c = 13.959(3) Å, ? = 104.99(3)°, and V = 1320.5(5) Å3 with Z = 4, for dcalc = 1.294 g/cm 3. Compound 2 is triclinic, of space group P1? with a = 6.877(3) Å, b = 7.590(5) Å, c = 13.213(9) Å, ? = 78.38(2)°, ? = 77.96(4)°, ? = 86.36(4)°, and V = 660.5(7) Å 3 with Z = 2, for dcalc = 1.294 g/cm3. Compound 3 is monoclinic, of space group P21/c with a = 12.604(2) Å, b = 15.592(3) Å, c = 6.875(2) Å, ? = 91.05(2)°, and V = 1350.9(2) Å3 with Z = 4, for dcalc = 1.265 g/cm3. The three thioureas are found in both solid state and solution in a conformation resulting from intramolecular N-H ? N hydrogen bonding. Compounds 1 and 3 present an intermolecular hydrogen bond involving the thione sulfur and the NH hydrogen, which is not present in 2 owing to the steric hindrance of the methyl group in the phenyl ring. The geometry of the molecule is affected by the position of the methyl groups on the pyridine and aryl rings.
Filiaciones:
Valdés-Martínez J.:
Instituto de Química, Univ. Nac. Auton. Mex. Circuito E., Ciudad Universitaria, Coyoacan 04510, Cd. Mexico DF, Mexico
Hernández-Ortega S.:
Instituto de Química, Univ. Nac. Auton. Mex. Circuito E., Ciudad Universitaria, Coyoacan 04510, Cd. Mexico DF, Mexico
Hermetet A.K.:
Department of Chemistry, Illinois State University, Normal, IL 61790-4160, United States
Ackerman L.J.:
Department of Chemistry, Illinois State University, Normal, IL 61790-4160, United States
Presto C.A.:
Department of Chemistry, Illinois State University, Normal, IL 61790-4160, United States
Swearingen J.K.:
Department of Chemistry, Illinois State University, Normal, IL 61790-4160, United States
Kelman D.R.:
Department of Chemistry, University of Washington, Seattle, WA 98195-1700, United States
Goldberg K.I.:
Department of Chemistry, University of Washington, Seattle, WA 98195-1700, United States
Kaminsky W.:
Department of Chemistry, University of Washington, Seattle, WA 98195-1700, United States
West D.X.:
Department of Chemistry, University of Washington, Seattle, WA 98195-1700, United States
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