Paradigms and paradoxes: Resonance stabilization in diazophenoxides (quinone diazides)

Structural Chemistry

Volumn 15, Issue 3, 2004, Pages 253-255

  Hosmane, Ramachandra S ^a   Liebman, Joel F ^a  

^a UNIVERSITY OF MARYLAND BALTIMORE COUNTY   (United States)

Author keywords

Diazocyclohexadienones; Enthalpies of combustion; Enthalpies of formation; o and p diazophenoxides; o and p quinone diazides; Resonance energy and stabilization

Indexed keywords

4 DIAZO 2,5 CYCLOHEXADIEN 1 ONE; AZIDE; AZO COMPOUND; DIAZOPHENOXIDE DERIVATIVE; OXIDE; QUINONE DIAZIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ENTHALPY; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 3543137852     PISSN: 10400400     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:STUC.0000021535.55038.32     Document Type: Article

References (19)

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2. (b) Sander, W.; Alberts, R.; Komnick, P.; Wandel, H. Liebigs Ann. Rec. 1997, p. 901.
3. This species, very often called diazodinitrophenol, dinol, diazol and D.D.N.P., is a long-known initiating explosive more powerful than mercury fulminate and slightly less than the commonly used lead azide. R. Meyer, Explosives, 2nd edn. Verlag Chemie, Weinheim, 1981.
4. Shiino, K. Oinuma, S. Kagaku Kogyo Shiryo 1984, 19, 136 (a review).
5. Glowiak, B. Chem. Stosow. 1961, 576.
6. With but the least of substitution, some of the annelation-related naphthalene species have found use as components of photoresists for microlithography, e.g., Dammel, R. Diazonaphthoquinone-Based Resists (Tutorial Texts in Optical Engineering, TT11, Society of Photo-optical Instrumentation Engineers); Bellingham, WA, 1993.
7. While this stability order is unequivocal in terms of kinetic stability, redox potentials of related o- and p-benzoquinones, and enthalpies of formation of the related naphthoquinones, there are seemingly no measured enthalpies of formation of any 1,2-benzoquinone.
8. See, for example, the discussion in Liebman, J. F. in The Chemistry of Functional Groups Supplement A2: The Chemistry of Dienes and Polyenes, Vol. 1; (Z. Rappoport, Ed.;), Wiley, Chichester, 1997; pp. 67-110.
9. -1 from the value in Ref. 4, we have ignored this value and its source hi the current study.
10. All otherwise unreferenced enthalpies of combustion (and enthalpies of formation) of all species in this paper are taken from the archive, Pedley, J. B; Naylor, R. D.; Kirby, S. P. Thermochemical Data of Organic Compounds; Chapman & Hall: New York, 1986.
11. There is a measurement for the enthalpy of combustion of trinitro species but we feel this species is so strained with its two vicinal nitro groups that it is atypical and so we do not wish to use the derived enthalpy of combustion difference of this species and the relatedly strained 1,2,4-trinitrobenzene.
12. The otherwise unreferenced enthalpies of fusion of all species in this paper are taken from the archive of Chickos. J. S.; Acree, W. E., Jr.; Liebman, J. F. J. Phys. Chem. Ref. Data, 1999, 28, 1535.
13. The value is taken from Ref. 9. We find ourselves in an interesting problem in choosing reference species for sublimation enthalpies. Suppose we suggest a more polar reference species, say 4-cyanopyridine-Wal-oxide, because of seemingly greater contribution of the dipolar benzenoid resonance structure. The stability of the gaseous diazophenol then decreases (its enthalpy of formation is higher) because the sublimation enthalpy connecting the derived value for the solid and desired gas is increased.
14. Skancke, A.; Hosmane, R. S.; Liebman, J. F. Acta Chem. Scand. 1998, 52, 967.
15. For a review of the thermochemistry of enones (both α, β-unsaturated ketones and also including aryl ketones) see Liebman, J. F.; Pollack, R. M. in The Chemistry of the Enone Functional Group S. Patai and Z. Rappoport, Eds; Wiley, Chichester, 1989; pp. 107-128.
16. The enthalpy of formation of diphenylmethane is taken from Steele, W. V.; Chirico, R. D.; Smith, N. K. J. Chem. Thermodyn. 1995, 27, 671.
17. Hartstock, F. W.; Kanabus-Kaminska, J. M.; Griller, D. Intern. J. Chem. Kinet. 1989, 21, 157.
18. 7itself, taken twice.)
19. Hosmane, R. S.; Liebman, J. F. Struct. Chem. 2002,13, 501.