Intra- and intermolecular hydrogen bonding and conformation in 1-acyl thioureas: An experimental and theoretical approach on 1-(2-chlorobenzoyl)thiourea

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

Volumn 143, Issue , 2015, Pages 59-66

  Saeed, Aamer ^a   Khurshid, Asma ^a   Bolte, Michael ^b   Fantoni, Adolfo C ^c   Erben, Mauricio F ^c  

^a QUAID I AZAM UNIVERSITY   (Pakistan)

^b GOETHE UNIVERSITY   (Germany)

^c UNIVERSIDAD NACIONAL DE LA PLATA   (Argentina)

Author keywords

AIM topological analysis; Crystal structure; Hydrogen bond; NBO; Thiourea; Vibrational spectroscopy

Indexed keywords

CONFORMATIONS; CRYSTAL STRUCTURE; MOLECULES; THIOUREAS; TOPOLOGY; VIBRATIONAL SPECTROSCOPY;

AIM TOPOLOGICAL; CONFORMATIONAL PROPERTIES; INTERMOLECULAR HYDROGEN BONDING; INTERMOLECULAR INTERACTIONS; INTRA-MOLECULAR HYDROGEN BONDS; INTRAMOLECULAR INTERACTIONS; NBO; X-RAY STRUCTURE DETERMINATIONS;

HYDROGEN BONDS;

1-(2-CHLOROBENZOYL)THIOUREA; THIOUREA;

ANALOGS AND DERIVATIVES; CHEMISTRY; CONFORMATION; HYDROGEN BOND; INFRARED SPECTROSCOPY; ISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; ISOMERISM; MOLECULAR CONFORMATION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; THIOUREA;

EID: 84923371473     PISSN: 13861425     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.saa.2015.02.042     Document Type: Article

References (72)

1. K.S. Eccles, R.E. Morrison, A.R. Maguire, and S.E. Lawrence Cryst. Growth Des. 14 2014 2753
2. E. Neucki Ber. Dtsch. Chem. Ges. 6 1873 598
3. K.R. Koch Coord. Chem. Rev. 216-217 2001 473
4. A.A. Aly, E.K. Ahmed, K.M. El-Mokadem, and M.E.-A.F. Hegazy J. Sulfur Chem. 28 2007 73
5. A. Saeed, U. Flörke, and M.F. Erben J. Sulfur Chem. 35 2014 318
6. Y.Y. Kharitonov, T.N. Gushchina, A.V. Gusev, and N.I. Kirillova Zh. Neorg. Khim. 33 1988 2228
7. S. Aruna, G. Shanmugam, S. Manogaran, and D.N. Sathyanarayana Bull. Chem. Soc. Jpn. 55 1982 3612
8. M.G. Woldu, and J. Dillen Theor. Chem. Acc. 121 2008 71
9. A.M. Plutín, H. Márquez, E. Ochoa, M. Morales, M. Sosa, L. Morán, Y. Rodríguez, M. Suárez, N. Martín, and C. Seoane Tetrahedron 56 2000 1533
10. A. Okuniewski, J. Chojnacki, and B. Becker Acta Crystallogr. E68 2012 o619
11. A. Saeed, and U. Flörke Acta Crystallogr. E63 2007 o3695
12. O. Estévez-Hernández, E. Otazo-Sánchez, J.L. Hidalgo-Hidalgo de Cisneros, I. Naranjo-Rodríguez, and E. Reguera Spectrochim. Acta A62 2005 964
13. H. Perez, R.S. Correa, A.M. Plutin, A. Alvarez, and Y. Mascarenhas Acta Crystallogr. E 67 2011 o647
14. H. Perez, R.S. Correa, A.M. Plutin, B. O'Reilly, and M.B. Andrade Acta Crystallogr. C 68 2012 o19
15. M. Boiocchi, L. Del Boca, D.E. Gomez, L. Fabbrizzi, M. Licchelli, and E. Monzani J. Am. Chem. Soc. 126 2004 16507
16. M. Bonizzoni, L. Fabbrizzi, A. Taglietti, and F. Tiengo Eur. J. Org. Chem. 2006 2006 3567
17. H.-L. Chen, Z.-F. Guo, and Z.-L. Lu Org. Lett. 14 2012 5070
18. S. Li, X. Cao, C. Chen, and S. Ke Spectrochim. Acta 96A 2012 18
19. A. Solinas, H. Faure, H. Roudaut, E. Traiffort, A. Schoenfelder, A. Mann, F. Manetti, M. Taddei, and M. Ruat J. Med. Chem. 55 2012 1559
20. C. Limban, A.-V. Missir, I.C. Chirita, A.F. Neagu, C. Draghici, and M.C. Chifiriuc Rev. Chim. (Bucharest) 62 2011 168
21. C. Limban, A.-V. Missir, I.C. Chirita, C.D. Badiceanu, C. Draghici, M.C. Balostescu, and O. Stamatoiu Rev. Roum. Chim. 53 2008 595
22. J. Müller, C. Limban, B. Stadelmann, A.V. Missir, I.C. Chirita, M.C. Chifiriuc, G.M. Nitulescu, and A. Hemphill Parasitol. Int. 58 2009 128
23. J. Sun, S. Cai, H. Mei, J. Li, N. Yan, Q. Wang, Z. Lin, and D. Huo Chem. Biol. Drug Des. 76 2010 245
24. X. Su, G. Zhang, T. Liu, L. Chen, J. Qin, and C. Chen Inorg. Chem. Commun. 9 2006 986
25. A. Saeed, M.F. Erben, U. Shaheen, and U. Flörke J. Mol. Struct. 1000 2011 49
26. A. Saeed, M.F. Erben, and M. Bolte J. Mol. Struct. 985 2010 57
27. M. Khawar Rauf, A. Badshah, and M. Bolte Acta Crystallogr. E 62 2006 o4084
28. A. Saeed, M.F. Erben, and U. Flörke J. Mol. Struct. 982 2010 91
29. M. Khawar Rauf, A. Badshah, A. Saeed, and M. Bolte Acta Crystallogr. E 62 2006 o1262
30. H. Arslan, N. Külcü, and U. Flörke Spectrochim. Acta 64A 2006 1065
31. H. Arslan, U. Flörke, N. Külcü, and G. Binzet Spectrochim. Acta 68A 2007 1347
32. A.E. Reed, R.B. Weinstock, and F. Weinhold J. Chem. Phys. 83 1985 735
33. J.P. Foster, and F. Weinhold J. Am. Chem. Soc. 102 1980 7211
34. R.F.W. Bader, J.R. Cheeseman, K.E. Laidig, K.B. Wiberg, and C. Brenemad J. Am. Chem. Soc. 112 1990 6530
35. I.B. Douglass, and F.B. Dains J. Am. Chem. Soc. 56 1934 719
36. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Jr. Montgomery, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople
37. M.J. Frisch, J.A. Pople, and J.S. Binkley J. Chem. Phys. 80 1984 3265
38. A. Fu, D. Du, and Z. Zhou Spectrochim. Acta 59A 2003 245
39. R. Dovesi, R. Orlando, B. Civalleri, C. Roetti, V.R. Saunders, and C.M. Zicovich-Wilson Z. Kristallogr. 220 2005 571
40. R. Dovesi, V.R. Saunders, C. Roetti, R. Orlando, C.M. Zicovich-Wilson, F. Pascale, B. Civalleri, K. Doll, N.M. Harrison, I.J. Bush, P. D'Arco, and M. Llunell CRYSTAL09 User's Manual 2009 University of Torino Torino
41. C. Gatti TOPOND 98 User's Manual 1999 CNR-ISTM Milano
42. A. Spek J. Appl. Crystallogr. 36 2003 7
43. G. Sheldrick Acta Crystallogr. A 64 2008 112
44. K. Gholivand, S. Farshadian, M.F. Erben, and C.O. Della Védova J. Mol. Struct. 978 2010 67
45. W. Yang, W. Zhou, and Z. Zhang J. Mol. Struct. 828 2007 46
46. F. Aydin, H. Ünver, D. Aykaç, and N.O. Iskeleli J. Chem. Crystallogr. 40 2010 1082
47. L. Adane, and P.V. Bharatam Int. J. Quantum Chem. 108 2008 1277
48. H. Arslan, D.S. Mansuroglu, D. VanDerveer, and G. Binzet Spectrochim. Acta 72A 2009 561
49. S.A. Slivko, Y.Y. Kharitonov, S.L. Kuznetsov, and T.N. Glushchina J. Struct. Chem. 34 1993 225
50. Z. Weiqun, L. Kuisheng, Z. Yong, and L. Lu J. Mol. Struct. 657 2003 215
51. Z. Weiqun, L. Baolong, Z. Baolong, D. Jiangang, Z. Yong, L. Lude, and Y. Xujie J. Mol. Struct. 690 2004 145
52. M. Atiş, F. Karipcin, B. SarIboʇa, M. Taş, and H. Çelik Spectrochim. Acta 98A 2012 290
53. O. Hritzová, J. Cernák, P. Safar, Z. Frohlichová, and I. Csoregh J. Mol. Struct. 743 2005 29
54. A. Saeed, M.F. Erben, and M. Bolte Spectrochim. Acta 102A 2013 408
55. W. Zhu, W. Yang, W. Zhou, H. Liu, S. Wei, and J. Fan J. Mol. Struct. 1004 2011 74
56. F. Karipcin, M. Atis, B. Sariboga, H. Celik, and M. Tas J. Mol. Struct. 1048 2013 69
57. K.J. Rothschild, I.M. Asher, H.E. Stanley, and E. Anastassakis J. Am. Chem. Soc. 99 1977 2032
58. O. Estévez-Hernández, E. Otazo-Sánchez, J.L.H.-H.d. Cisneros, I. Naranjo-Rodríguez, and E. Reguera Spectrochim. Acta A64 2006 961
59. N. Selvakumaran, M.M. Sheeba, R. Karvembu, S.W. Ng, and E.R.T. Tiekink Acta Crystallogr. E 68 2012 o3259
60. N. Gunasekaran, P. Jerome, R. Karvembu, S.W. Ng, and E.R.T. Tiekink Acta Crystallogr. E 67 2011 o1149
61. B.M. Yamin, and E.A. Othman Acta Crystallogr. E 64 2008 o313
62. I.N. Hassan, B.M. Yamin, and M.B. Kassim Acta Crystallogr. E 66 2010 o2796
63. E. Espinosa, M. Souhassou, H. Lachekar, and C. Lecomte Acta Crystallogr. B 55 1999 563
64. J. Bernstein, M.C. Etter, and L. Leiserowitz The Role of Hydrogen Bonding in Molecular Assemblies 2008 Wiley-VCH Verlag GmbH
65. A.G. Dikundwar, U.D. Pete, C.M. Zade, R.S. Bendre, and T.N. Guru Row Cryst. Growth Des. 12 2012 4530
66. L.R. Gomes, L.M.N.B.F. Santos, J.A.P. Coutinho, B. Schroder, and J.N. Low Acta Crystallogr. E 66 2010 o870
67. U. Adhikari, and S. Scheiner J. Phys. Chem. A 116 2012 3487
68. A.J. Lopes Jesus, M.T.S. Rosado, I. Reva, R. Fausto, M.E.S. Eusébio, and J.S. Redinha J. Phys. Chem. A 112 2008 4669
69. A.E. Reed, L.A. Curtiss, and F. Weinhold Chem. Rev. 88 1988 899
70. A. Saeed, A. Khurshid, J.P. Jasinski, C.G. Pozzi, A.C. Fantoni, and M.F. Erben Chem. Phys. 431-432 2014 39
71. L. Aguilar-Castro, M. Tlahuextl, L.H. Mendoza-Huizar, A.R. Tapia-Benavides, and H. Tlahuext ARKIVOC 2008 210
72. G.R. Desiraju Acc. Chem. Res. 35 2002 565