Intermolecular complexes of halocyclopropenone derivatives with the hypohalous acids HOF, HOCl, HOBr, and HOI

The intermolecular interactions between halocyclopropenone derivatives (HC3 OX; X = I, Br, Cl, and F)and hypohalous acids (HOY; Y = I, Br, Cl, and F) were studied via the MP2 method utilizing the aug-cc-pVTZand aug-cc-pVTZ(-PP) basis sets. The three types of complexes were hydrogen bonds, halogen bonds, and complexescontaining both hydrogen and halogen bonds. The results obtained indicated that interactions in the Type 1 complexeswere stronger than those in Types 2 and 3. The H–O bonds revealed red shifts with complex formation in Types 1 and2. The O–Y bonds displayed red shifts in the Type 3 and blue shifts in the Type 2 structures. Molecular electrostaticpotential, quantum theory of atoms in molecules, and natural bond orbital methodologies were used to analyze theseinteractions.

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1. Okuda, T.; Yoneyama, Y.; Fujiwara, A.; Furumai, T. J. Antibiotics 1984, 37, 712-717.
2. Sakaki, S.; Musashi, S.; Ohkubo, K. J. Am. Chem. Soc. 1993, 115, 1515-1519.
3. Liu, L.; Xia, S.; Fang, W. H. J. Phys. Chem. A 2014, 118, 8977-8985.
4. Breslow, R.; Oda, M. J. Am. Chem. Soc. 1972, 94, 8647-8647.
5. Komatsu, K.; Kitagawa, T. Chem. Rev. 2003, 103, 1371-1428.
6. Elrob, S. A. Y.; Osman, O. I.; Aziz, S. G. Mol. Phys. 2011, 109, 1785-1795.
7. Ahmadvand, S.; Zaari, R. R.; Varganov, S. A. Astrophys. J. 2014, 795, 173-178.
8. Poloukhtine, A.; Popik, V. V. M. J. Phys. Chem. A 2006, 110, 1749-1757.
9. Fitzpatrick, N.; Fanning, M. J. Mol. Struct. 1976, 33, 257-263.
10. Werz, D. B.; Klatt, G. N.; Raskatov, J. A.; Ko¨ppel, H.; Gleiter, R. Organometallics 2009, 28, 1675-1682.
11. Nguyen, L. T.; Proft, F. De.; Nguyen, M. T.; Geerlings, P. J. Chem. Soc. Chem. Commun.2001, 2, 898-905.
12. Nguyen, L. T.; Proft, F. De.; Nguyen, M. T.; Geerlings, P. J. Org. Chem. 2001, 66, 4316-4326.
13. Hobza, P.; Müller-Dethlefs, K. Roy. Soc. Ch. 2010, 2, 1-20.
14. Raju, R. K.; Bloom, J. W. G.; An, Y.; Wheeler, S. E. ChemPhysChem. 2011, 12, 3116-3130.
15. Seth, S. K.; Manna, P.; Singh, N. J.; Mitra, M.; Jana, A. D.; Das, A.; Choudhury, S. R.; Kar, T.; Mukhopadhyay, S.; Kim, K. S. CrystEngComm. 2013, 15, 1285-1288.
16. Alberto, M. E.; Mazzone, G.; Russo, N.; Sicilia, E. J. Chem. Soc. Chem. Commun. 2010, 46, 5894-5896.
17. Černý, J.; Hobza, P. Phys. Chem. Chem. Phys. 2007, 9, 5291-5303.
18. Mohan, N.; Suresh, C. H. J. Phys. Chem. 2014, 118, 1697-1705.
19. Grabowski, S. J. Phys. Chem. Chem. Phys. 2013, 15, 7249-7259.
20. Vatanparast, M. Comput. Theor. Chem. 2014, 1048, 77-83.
21. Wilcken, R.; Zimmermann, M. O.; Lange, A.; Joerger, A. C.; Boeckler, F. M. J. Med. Chem. 2013, 56, 1363-1388.
22. Shiraga, K.; Adachi, A.; Nakamura, M.; Tajima, T.; Ajito, K.; Ogawa, Y. J. Chem. Phys. 2017, 146, 102-105.
23. Vatanparast, M.; Taghizadeh, M. T.; Parvini, E. J. Theor. Comput. Chem. 2015, 14, 1550046-1550060.
24. Zabardasti, A.; Solimannejad, M. J. Mol. Struct: THEOCHEM. 2007, 819, 52-59.
25. Zabardasti, A.; Zare, N.; Arabpour, M. Struct. Chem. 2011, 22, 691-695.
26. Politzer, P.; Murray, J.; Clark, T. Phys. Chem. Chem. Phys. 2010, 12, 7748-7757
27. Metrangolo, P.; Murray, J. S.; Pilati, T.; Politzer, P.; Resnati, G.; Terraneo, G. Cryst. Growth 2011, 11, 4238-4246.
28. Valerio, G.; Raos, G.; Meille, S. V.; Metrangolo, P.; Resnati, G. J. Phys. Chem. A 2000, 104, 1617-1620.
29. Arunan, E.; Desiraju, G. R.; Klein, R. A.; Sadlej, J.; Scheiner, S.; Alkorta, S. I.; Clary, D. C.; Crabtree, R. H.; Dannenberg, J. J.; Hobza, P.; et al. Pure Appl. Chem. 2011, 83, 1619-1627.
30. Li, Q.; Zhu, H.; Zhuo, H.; Yang, X.; Li, W.; Cheng, J. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2014, 132, 271-277.
31. Li, Q.; Xu, X.; Liu, T.; Jing, B.; Li, W.; Cheng, J; Gong, B; Sun, J. Phys. Chem. Chem. Phys. 2010, 12, 6837-6843.
32. Sanchez-Sanz, G.; Trujillo, C.; Alkorta, I.; Elguero, J. Phys. Chem. Chem. Phys. 2012, 14, 9880-9889.
33. An, X.; Yang, X.; Xiao, B.; Cheng, J.; Li, Q. Mol Phys. 2017, 115, 1614-1623.
34. Blanco, F.; Alkorta, I.; Solimannejad, M.; Elguero, J. J. Phys. Chem. A 2009, 113, 3237-3244.
35. Ghanty, T. K.; Ghosh, S. K. J. Phys. Chem. A 1997, 27, 5022-5025.
36. Zabardasti, A.; Sharifi-rad, A.; Kakanejadifard, A. Spectrochim. Acta A 2015, 151, 746-759.
37. Li, Q.; Zhu, H.; Yang, X.; Li, W.; Cheng, J. Spectrochim. Acta A 2014, 132, 271-277.
38. Alkorta, I.; Blanco, F.; Solimannejad, M.; Elguero, J. J.Phys. Chem. A 2008, 112, 10856-10863.
39. Zabardasti, A.; Kakanejadifard, A.; Goudarziafshar, H.; Salehnassaj, M.; Zohrehband, Z.; Jaberansari, F.; Solimannejad, M. Comput. Theor. Chem. 2013, 1014, 1-7.
40. Bader, R. F. W. Atoms in Molecules: a Quantum Theory. Clarendon: Oxford, UK, 1990.
41. Politzer, P.; Murray, J. S. Phys. Chem. Chem. Phys. 2013, 15, 11178-11189.
42. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.
43. Sánchez-Sanz, G.; Trujillo, C.; Solimannejad, M.; Alkorta, I.; Elguero, J. Phys. Chem. Chem. Phys. 2013, 15, 14310-14318.
44. Bondi, A. J. Phys. Chem. 1964, 68, 441-451.
45. Ziółkowski, M.; Grabowski, S. J.; Leszczynski, J. J. Phys. Chem. A 2006, 110, 6514-6521.
46. Zhang, X.; Li, X.; Zeng, Y.; Meng, L.; Zheng, S. Int. J. Quantum. Chem. 2014, 114, 400-408.
47. Rozas, I.; Alkorta, I.; Elguero, J. J. Am. Chem. Soc. 2000, 122, 11154-11161.
48. Frisch, M.; Trucks, G; Schlegel, H.; Scuseria, G.; Robb, M.; Cheeseman, J.; Montgomery Jr, J.; Vreven, T.; Kudin, K.; Burant, J. Gaussian 03, revision c. 02; Gaussian, Inc.: Wallingford, CT, USA, 2004.
49. Cremer, D. Comput. Mol. Sci. 2011, 1, 509-530.
50. Esrafili, M. D.; Mohammadirad, N. J. Mol. Model. 2013, 19, 2559-2566.
51. Esrafili, M. D.; Solimannejad, M. N. J. Mol. Model. 2013, 19, 3767-3774.
52. Boys, S. F.; Bernardi, F. D. Mol. Phys. 1970, 19, 553-566.
53. Bulat, F. A.; Toro-Labbé, A.; Brinck, T.; Murray, J. S.; Politzer, P. J. Mol. Model. 2010, 16, 1679-1691.
54. Biegler Konig, F.; Schonbohm, J. J. Comput. Chem. 2001, 22, 545-559.
55. Glendening, E. D.; Weinhold, F. J. Comput. Chem. 1998, 19, 593-609.