|
|
|
Determination of NO chemical affinities of benzyl
nitrite in acetonitrile |
| LI Xin, ZHU Xiaoqing, CHENG Jinpei |
| State Key Laboratory of Elemento-Organic Chemistry, Department of Chemistry, Nankai University |
|
|
|
|
Abstract There is an increasing interest in the study of NO chemical affinities of organic nitrites, for the biological and physiological effects of organic nitrites seem to be due to their ability to release NO. In this paper, NO chemical affinities of ten substituted benzyl nitrites were determined by titration calorimetry combined with a thermodynamic cycle in acetonitrile solution. The results show that ?Hhet(O–NO)s of benzyl nitrites are substantially larger than the corresponding ?Hhomo(O–NO)s, suggesting that these O-nitroso compounds much more easily release NO radicals by the O–NO bond homolytic cleavage. It is believed that the structural and energetic information disclosed in this work should be useful in understanding chemical and biological functions of organic nitrites.
|
|
Issue Date: 05 December 2008
|
|
| 1 |
Cederqvist B, Persson M G, Gustafsson L E . Direct demonstration of NO formation in vivo from organic nitrites and nitrates, and correlationto effects on blood pressure and to in vitro effects. Biochem Pharmacol, 1994, 47(6): 1047–1053.
doi:10.1016/0006-2952(94)90416-2
|
| 2 |
Wang P G, Xian M, Tang X, Wu X, Wen Z, Cai T, Janczuk A J . Nitric oxide donors: chemical activitiesand biological applications. Chem Rev, 2002, 102: 1091–1134.
doi:10.1021/cr000040l
|
| 3 |
Kielbasa W, Fung H L . Nitrite inhalation in ratselevates tissue NOS III Expression and alters tyrosine nitration andphosphorylation. Biochem Biophys Res Commun, 2000, 275: 335–342
|
| 4 |
Nicolescu A C, Reynolds J N, Barclay L R C, Thatcher G R J . Organic nitrites and NO: inhibition of lipid peroxidation and radicalreactions. Chem Res Toxicol, 2004, 17: 185–196
|
| 5 |
Doel J J, Godber B L J, Goult T A, Eisenthal R, Harrison R . Reduction of organic nitritesto nitric oxide catalyzed by xanthine oxidase: possible role in metabolismof nitrovasodilators. Biochem Biophys ResCommun, 2000, 270: 880–885
|
| 6 |
Cheng J P, Xian M, Wang K, Zhu X Q, Yin Z, Wang P G . Heterolyticand homolytic Y–NO bond energy scales of nitroso-containingcompounds: chemical origin of NO release and NO capture. J Am Chem Soc, 1998, 120: 10266–10267.
doi:10.1021/ja982086q
|
| 7 |
Xian M, Zhu X Q, Lu J, Wen Z, Cheng J P . The first O–NO bond energy scalesin solution: heterolytic and homolytic cleavage enthalpies of O-Nitroso carboxylate compounds org Lett, 2000, 2: 265–268
|
| 8 |
Zhu X Q, He J Q, Xian M, Cheng J P . Heterolyticand homolytic N–NO bond dissociation energies of N-nitroso compounds and their radical anions:implications for the effect of reductive electron transfer on bondactivation and for the mechanisms of NO transfer to nitranions. J Org Chem, 2000, 65: 6729–6735.
doi:10.1021/jo000865v
|
| 9 |
Lu J M, Wittbrodt J M, Wang K, Wen Z, Schlegel H B, Wang P G, Cheng J P . NO affinities of S-nitrosothiols: A direct experimental andcomputational investigation of RS–NO bond dissociation energies. J Am Chem Soc, 2001, 123: 2903–2904.
doi:10.1021/ja000384t
|
| 10 |
Zhu X Q, Hao W F, Tang H, Wang C H, Cheng J P . Determination of N–NO bond dissociationenergies of N-Methyl-N-nitrosobenzenesulfonamides in acetonitrileand application in the mechanism analyses on NO transfer. J Am Chem Soc, 2005, 127: 2696–2708.
doi:10.1021/ja0443676
|
| 11 |
Arnett E M, Amarnath K, Harvey N G, Cheng J P . Chemicalbond-making, bond-breaking, and electron transfer in solution. Science, 1990, 247: 423–430.
doi:10.1126/science.247.4941.423
|
| 12 |
Hansch C, Leo A, Taft R W . A survey of hammett substituent constants and resonanceand field parameters. Chem Rev, 1991, 91: 165–195.
doi:10.1021/cr00002a004
|
|
Viewed |
|
|
|
Full text
|
|
|
|
|
Abstract
|
|
|
|
|
Cited |
|
|
|
|
| |
Shared |
|
|
|
|
| |
Discussed |
|
|
|
|
