Solid-state reaction mechanisms in monomer-dimer interconversions of p-bromonitrosobenzene. Single-crystal-to-single-crystal photodissociation and formation of new non-van der Waals close contacts

Journal of Organic Chemistry

Volumn 70, Issue 21, 2005, Pages 8461-8467

  Halasz, Ivan ^a   Mestrovic, Ernest ^a   Cicak, Helena ^a   Mihalic, Zlatko ^a   Vancik, Hrvoj ^a  

^a UNIVERSITY OF ZAGREB   (Croatia)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; BROMINE COMPOUNDS; DIMERIZATION; DIMERS; PHASE TRANSITIONS; PHOTOCHEMICAL REACTIONS; PHOTODISSOCIATION; REACTION KINETICS; SINGLE CRYSTALS;

FIRST-ORDER KINETICS; P-BROMONITROBENZENE; SINGLE CRYSTAL-TO-SINGLE-CRYSTAL TRANSFORMATION; SOLID-STATE REACTION MECHANISM;

MONOMERS;

4 BROMONITROSOBENZENE; DIMER; MONOMER; NITROGEN; OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DIMERIZATION; DISSOCIATION; LOW TEMPERATURE; MOLECULAR INTERACTION; PHASE TRANSITION; SOLID STATE; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE; THERMAL ANALYSIS;

EID: 26844558034     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051236u     Document Type: Article

References (22)

1. Schmidt, G. M. J. et al. Solid State Photochemistry; Ginsburg, D., Ed.; Verlag Chemie: Weinheim, New York, 1976; p 80.
2. Brown, M. E.; Dollimore, D.; Galwey, A. K. Comprehensive Chemical Kinetics; Elsevier: Amsterdam, 1980; Vol. 22.
3. Skrdla, P. J. J. Phys. Chem. A 2004, 108, 6709-6712.
4. Galwey, A. K. Thermochim. Acta 2004, 413, 139-183.
5. Kim, J. H.; Hubig, S. M.; Lindeman, S. U.; Kochi, J. K. J. Am. Chem. Soc. 2001, 123, 87-95.
6. (a) Vancik, H.; Simunic-Meznaric, V.; Mestrovic, E.; Halasz, I. J. Org. Chem. 2004, 69, 4829-4834.
7. ms1) of the reaction could convert to 50%. However, the complete thermal reaction that includes also a long period of the phase transformation led to the complete dimerization.
8. Vancik, H.; Simunic-Meznaric, V.; Caleta, I.; Mestrovic, E.; Milovac, S.; Mlinaric Majerski, K.; Veljkovic, J. J. Phys. Chem. B 2002, 106, 1576-1580.
9. (a) Webster, M. S. J. Chem. Soc. 1956, 2841.
10. (b) Talberg, H. J. Acta Chem. Scand. A 1979, 33, 289.
11. (a) Desiraju, G. R. Crystal Engineering. The Design of Organic Solids; Elsevier: Amsterdam, 1989; pp 92, 144.
12. (b) Capiomont, A.; Chion, B.; Lajzerowicz, J. Acta Crystallogr., Sect. B 1971, 27, 322.
13. (c) Yoon, K.; Parkin, G.; Rheingold, A. L. J. Am. Chem. Soc. 1991, 113, 1437-1438.
14. (d) Parkin, G. Acc. Chem. Res. 1992, 25, 455-460.
15. Sheldrick, G. M. SHELXL93-Program for Crystal Structure Refinement; Institut für Anorganische Chemie der Universität: Göttingen, Germany, 1993.
16. Farrugia, L. J., J. Appl. Crystallogr. 1999, 32, 837-838.
17. Bruno, I. J.; Cole, J. C.; Edgington, P. R. Kessler, M.; Macrae, C. F. McCabe, P.; Pearson, J.; Taylor, R. Acta Crystallogr. 2002, B58, 389-387.
18. Kiger, P. Fl.; Thi, H. P. L.; Portmann, S.; Weber, J. Swiss Center for Scientific Computing, Manno (Switzerland), 2000.
19. Koch, W.; Holthausen, M. C. A Chemist's Guide to Density Functional Theory; Wiley-VCH: Weinheim, 2000.
20. Hehre, W. J.; Radom, L.; Schleyer, P. von R.; Pople, J. A. Ab initio Molecular Orbital Theory; John Wiley & Sons: New York, 1986.
21. Jensen, F. Introduction to Computational Chemistry; John Wiley & Sons: Canada, 1999.
22. Gaussian 03, Revision C.02; Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Kiene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian, Inc.: Wallingford CT, 2004.