Revised structure of a purported 1,2-dioxin: A combined experimental and theoretical study

Journal of Organic Chemistry

Volumn 68, Issue 10, 2003, Pages 4108-4111

  Block, Eric ^a   Shan, Zhixing ^a   Glass, Richard S ^b   Fabian, Jürgen ^c  

^a STATE UNIVERSITY OF NEW YORK   (United States)

^b UNIVERSITY OF ARIZONA   (United States)

^c DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULAR STRUCTURE; PHOTOCHEMICAL REACTIONS; POSITIVE IONS;

ELECTRON TRANSFER;

ORGANIC COMPOUNDS;

1,2 DIOXIN; DIOXIN; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERISM; PHOTOCHEMISTRY; REACTION ANALYSIS; STRUCTURE ANALYSIS; THERMODYNAMICS;

EID: 0037612526     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034305i     Document Type: Article

References (36)

1. For key references, see: (a) Block, E.; Birringer, M.; DeOrazio, R.; Fabian, J.; Glass, R. S.; Guo, C.; He, C.; Lorance, E.; Qian, Q.; Schroeder, T. B.; Shan, Z.; Thiruvazhi, M.; Wilson, G. S.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 5052-5064.
2. (b) Glass, R. S.; Gruhn, N. E.; Lichtenberger, D. L.; Lorance, E.; Pollard, J. R.; Birringer, M.; Block, E.; DeOrazio, R.; He, C.; Shan, Z.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 5065-5074.
3. (c) Wakamiya, A.; Nishinaga, T.; Komatsu, K. J. Am. Chem. Soc. 2002, 142, 15038-15050.
4. Block, E.; Birringer, M.; He, C., Angew. Chem., Int. Ed. 1999, 38, 1604-1607.
5. (a) Gillies, J. Z.; Gillies, C. W.; Cotter, E. A.; Block, E.; DeOrazio, R. J. Mol. Spectrosc. 1996, 180, 139-144.
6. (b) Gillies, J. Z.; Gillies, C. W.; Nathan, C.; Zhang, Y.; Block, E. Manuscript in preparation.
7. Shine, H. J.; Zhao, D.-C. J. Org. Chem. 1990, 55, 4086-4089.
8. In addition, a transient but trappable 1,4-diphenyl-2,3-benzodioxin has also been reported: Smith, J. P.; Schrock, A. K.; Schuster, G. B. J. Am. Chem. Soc. 1982, 104, 1041-1047.
9. (a) Conant, J. B.; Lutz, R. E. J. Am. Chem. Soc. 1923, 45, 1303-1307.
10. (b) Freeman, F.; Lee, M. Y.; Lu, H.; Wang, X.; Rodriguez, E. J. Org. Chem. 1994, 59, 3695-3698.
11. Previous theoretical studies on 1c-e and derivatives: (a) Cimiraglia, R.; Fabian, J.; Hess, B. A., Jr. J. Mol. Struct. (THEOCHEM) 1991, 230, 287-293. (b) Mann, M.; Fabian, J. J. Mol. Struct. (THEOCHEM) 1995, 331, 51-61. (c) Pitchko, V.; Goddard, J. D. Chem. Phys. Lett. 1998, 289, 391-5. (d) Ishida, T.; Oe, S.; Aihara, J. J. Mol. Struct. (THEOCHEM) 1999, 461-2, 553-559. (e) Aihara, J.; Ishida, T. Bull. Chem. Soc. Jpn. 1999, 72, 937-941. (f) Orlova, G.; Goddard, J. D. J. Chem. Phys. 2000, 112, 10085-10094. (g) Fabian, J.; Mann, M.; Petiau, M. J. Mol. Model 2000, 6, 177-185. (h) Ortiz, J. V. J. Phys. Chem. A 2002, 106, 5924-5927.
12. Previous theoretical studies on 1c-e and derivatives: (a) Cimiraglia, R.; Fabian, J.; Hess, B. A., Jr. J. Mol. Struct. (THEOCHEM) 1991, 230, 287-293. (b) Mann, M.; Fabian, J. J. Mol. Struct. (THEOCHEM) 1995, 331, 51-61. (c) Pitchko, V.; Goddard, J. D. Chem. Phys. Lett. 1998, 289, 391-5. (d) Ishida, T.; Oe, S.; Aihara, J. J. Mol. Struct. (THEOCHEM) 1999, 461-2, 553-559. (e) Aihara, J.; Ishida, T. Bull. Chem. Soc. Jpn. 1999, 72, 937-941. (f) Orlova, G.; Goddard, J. D. J. Chem. Phys. 2000, 112, 10085-10094. (g) Fabian, J.; Mann, M.; Petiau, M. J. Mol. Model 2000, 6, 177-185. (h) Ortiz, J. V. J. Phys. Chem. A 2002, 106, 5924-5927.
13. Previous theoretical studies on 1c-e and derivatives: (a) Cimiraglia, R.; Fabian, J.; Hess, B. A., Jr. J. Mol. Struct. (THEOCHEM) 1991, 230, 287-293. (b) Mann, M.; Fabian, J. J. Mol. Struct. (THEOCHEM) 1995, 331, 51-61. (c) Pitchko, V.; Goddard, J. D. Chem. Phys. Lett. 1998, 289, 391-5. (d) Ishida, T.; Oe, S.; Aihara, J. J. Mol. Struct. (THEOCHEM) 1999, 461-2, 553-559. (e) Aihara, J.; Ishida, T. Bull. Chem. Soc. Jpn. 1999, 72, 937-941. (f) Orlova, G.; Goddard, J. D. J. Chem. Phys. 2000, 112, 10085-10094. (g) Fabian, J.; Mann, M.; Petiau, M. J. Mol. Model 2000, 6, 177-185. (h) Ortiz, J. V. J. Phys. Chem. A 2002, 106, 5924-5927.
14. Previous theoretical studies on 1c-e and derivatives: (a) Cimiraglia, R.; Fabian, J.; Hess, B. A., Jr. J. Mol. Struct. (THEOCHEM) 1991, 230, 287-293. (b) Mann, M.; Fabian, J. J. Mol. Struct. (THEOCHEM) 1995, 331, 51-61. (c) Pitchko, V.; Goddard, J. D. Chem. Phys. Lett. 1998, 289, 391-5. (d) Ishida, T.; Oe, S.; Aihara, J. J. Mol. Struct. (THEOCHEM) 1999, 461-2, 553-559. (e) Aihara, J.; Ishida, T. Bull. Chem. Soc. Jpn. 1999, 72, 937-941. (f) Orlova, G.; Goddard, J. D. J. Chem. Phys. 2000, 112, 10085-10094. (g) Fabian, J.; Mann, M.; Petiau, M. J. Mol. Model 2000, 6, 177-185. (h) Ortiz, J. V. J. Phys. Chem. A 2002, 106, 5924-5927.
15. Previous theoretical studies on 1c-e and derivatives: (a) Cimiraglia, R.; Fabian, J.; Hess, B. A., Jr. J. Mol. Struct. (THEOCHEM) 1991, 230, 287-293. (b) Mann, M.; Fabian, J. J. Mol. Struct. (THEOCHEM) 1995, 331, 51-61. (c) Pitchko, V.; Goddard, J. D. Chem. Phys. Lett. 1998, 289, 391-5. (d) Ishida, T.; Oe, S.; Aihara, J. J. Mol. Struct. (THEOCHEM) 1999, 461-2, 553-559. (e) Aihara, J.; Ishida, T. Bull. Chem. Soc. Jpn. 1999, 72, 937-941. (f) Orlova, G.; Goddard, J. D. J. Chem. Phys. 2000, 112, 10085-10094. (g) Fabian, J.; Mann, M.; Petiau, M. J. Mol. Model 2000, 6, 177-185. (h) Ortiz, J. V. J. Phys. Chem. A 2002, 106, 5924-5927.
16. Previous theoretical studies on 1c-e and derivatives: (a) Cimiraglia, R.; Fabian, J.; Hess, B. A., Jr. J. Mol. Struct. (THEOCHEM) 1991, 230, 287-293. (b) Mann, M.; Fabian, J. J. Mol. Struct. (THEOCHEM) 1995, 331, 51-61. (c) Pitchko, V.; Goddard, J. D. Chem. Phys. Lett. 1998, 289, 391-5. (d) Ishida, T.; Oe, S.; Aihara, J. J. Mol. Struct. (THEOCHEM) 1999, 461-2, 553-559. (e) Aihara, J.; Ishida, T. Bull. Chem. Soc. Jpn. 1999, 72, 937-941. (f) Orlova, G.; Goddard, J. D. J. Chem. Phys. 2000, 112, 10085-10094. (g) Fabian, J.; Mann, M.; Petiau, M. J. Mol. Model 2000, 6, 177-185. (h) Ortiz, J. V. J. Phys. Chem. A 2002, 106, 5924-5927.
17. Previous theoretical studies on 1c-e and derivatives: (a) Cimiraglia, R.; Fabian, J.; Hess, B. A., Jr. J. Mol. Struct. (THEOCHEM) 1991, 230, 287-293. (b) Mann, M.; Fabian, J. J. Mol. Struct. (THEOCHEM) 1995, 331, 51-61. (c) Pitchko, V.; Goddard, J. D. Chem. Phys. Lett. 1998, 289, 391-5. (d) Ishida, T.; Oe, S.; Aihara, J. J. Mol. Struct. (THEOCHEM) 1999, 461-2, 553-559. (e) Aihara, J.; Ishida, T. Bull. Chem. Soc. Jpn. 1999, 72, 937-941. (f) Orlova, G.; Goddard, J. D. J. Chem. Phys. 2000, 112, 10085-10094. (g) Fabian, J.; Mann, M.; Petiau, M. J. Mol. Model 2000, 6, 177-185. (h) Ortiz, J. V. J. Phys. Chem. A 2002, 106, 5924-5927.
18. Previous theoretical studies on 1c-e and derivatives: (a) Cimiraglia, R.; Fabian, J.; Hess, B. A., Jr. J. Mol. Struct. (THEOCHEM) 1991, 230, 287-293. (b) Mann, M.; Fabian, J. J. Mol. Struct. (THEOCHEM) 1995, 331, 51-61. (c) Pitchko, V.; Goddard, J. D. Chem. Phys. Lett. 1998, 289, 391-5. (d) Ishida, T.; Oe, S.; Aihara, J. J. Mol. Struct. (THEOCHEM) 1999, 461-2, 553-559. (e) Aihara, J.; Ishida, T. Bull. Chem. Soc. Jpn. 1999, 72, 937-941. (f) Orlova, G.; Goddard, J. D. J. Chem. Phys. 2000, 112, 10085-10094. (g) Fabian, J.; Mann, M.; Petiau, M. J. Mol. Model 2000, 6, 177-185. (h) Ortiz, J. V. J. Phys. Chem. A 2002, 106, 5924-5927.
19. (a) Curtiss L. A.; Ragahavachari, K. In Encyclopedia of Computational Chemistry; Schleyer P. v. R., Ed.; Wiley: Chichester, UK, 1998; Vol. 2, p 1104-1114.
20. G2(MP2) is a composite technique of ab initio quantum chemical calculations used to obtain accurate energies of molecular systems. Optimum geometry and energy were calculated by MP2/6-31G and two single-point calculations, MP2/6-311+CT(3df, 2p) and QCISD(T)/6-311G(d, p)
21. Koch, W.; Holthausen, M. C. A Chemist's Guide to Density Functional Theory; Wiley-VCH: Weinheim, Germany, 2000.
22. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 1372-1377.
23. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785-789.
24. (c) For implementation of B3-LYP in GAUSSIAN, see: Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627.
25. f by MINDO/3 is 51.5 kcal/mol: Pichko, V. A.; Simkin, B. Ya.; Minkin, V. I. J. Org. Chem. 1992, 57, 7087-7092.
26. Bally, T.; Borden, W. T. Rev. Comput. Chem. 1999, 13, 1-97 and references therein.
27. 5
28. (a) Gill, M. W.; Radom, L. J. Am. Chem. Soc. 1988, 110, 4931-4941.
29. (b) But also see: Maity, D. K. J. Phys. Chem. A 2002, 106, 5716-5721.
30. Boden, N.; Borner, R.; Bushby, R. J.; Clements, J. Tetrahedron Lett. 1991, 32, 6195-6198.
31. Schaftenaar, G. MOLDEN, Release 3.5; CMBI: Nijmegen, 1999.
32. Wiberg, K. B. Tetrahedron 1968, 24, 1083-1096.
33. (a) Glendening, E. D.; Weinhold F. J. Comput. Chem. 1998, 19, 593-609.
34. (b) Glendening, E. D.; Weinhold F. J. Comput. Chem. 1998, 19, 610-627.
35. Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. Program Package NBO 4.M; Theoretical Chemistry Institute, University of Wisconsin: Madison, WI, 1996.
36. Calculations were performed with the GAUSSIAN 98 suite of programs: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.