The Structure and Conformation of (CH3)(3)CSNO

Canneva A, Erben MF, Romano RM, Vishnevskiy Y, Reuter C, Mitzel NW, Della Vedova CO (2015)
Chemistry - A European Journal 21(29): 10436-10442.

Download
Es wurde kein Volltext hochgeladen. Nur Publikationsnachweis!
Zeitschriftenaufsatz | Veröffentlicht | Englisch
Autor
; ; ; ; ; ;
Abstract / Bemerkung
The gas-phase molecular structure of (CH3)(3)CSNO was investigated by using electron diffraction, allowing the first experimental geometrical parameters for an S-nitrosothiol species to be elucidated. Depending on the orientation of the SNO group, two conformers (anti and syn) are identified in the vapor of (CH3)(3)CSNO at room temperature, the syn conformer being less abundant. The conformational landscape is further scrutinized by using vibrational spectroscopy techniques, including gas-phase and matrix-isolation IR spectroscopy, resulting in a contribution of ca. 80:20 for the anti:syn abundance ratio, in good agreement with the computed value at the MP2(full)/cc-pVTZ level of approximation. The UV/Vis and resonance Raman spectra also show the occurrence of the conformational equilibrium in the liquid phase, with a moderate post-resonance Raman signature associated with the 350nm electronic absorption.
Erscheinungsjahr
Zeitschriftentitel
Chemistry - A European Journal
Band
21
Ausgabe
29
Seite(n)
10436-10442
ISSN
PUB-ID

Zitieren

Canneva A, Erben MF, Romano RM, et al. The Structure and Conformation of (CH3)(3)CSNO. Chemistry - A European Journal. 2015;21(29):10436-10442.
Canneva, A., Erben, M. F., Romano, R. M., Vishnevskiy, Y., Reuter, C., Mitzel, N. W., & Della Vedova, C. O. (2015). The Structure and Conformation of (CH3)(3)CSNO. Chemistry - A European Journal, 21(29), 10436-10442. doi:10.1002/chem.201500811
Canneva, A., Erben, M. F., Romano, R. M., Vishnevskiy, Y., Reuter, C., Mitzel, N. W., and Della Vedova, C. O. (2015). The Structure and Conformation of (CH3)(3)CSNO. Chemistry - A European Journal 21, 10436-10442.
Canneva, A., et al., 2015. The Structure and Conformation of (CH3)(3)CSNO. Chemistry - A European Journal, 21(29), p 10436-10442.
A. Canneva, et al., “The Structure and Conformation of (CH3)(3)CSNO”, Chemistry - A European Journal, vol. 21, 2015, pp. 10436-10442.
Canneva, A., Erben, M.F., Romano, R.M., Vishnevskiy, Y., Reuter, C., Mitzel, N.W., Della Vedova, C.O.: The Structure and Conformation of (CH3)(3)CSNO. Chemistry - A European Journal. 21, 10436-10442 (2015).
Canneva, Antonela, Erben, Mauricio F., Romano, Rosana M., Vishnevskiy, Yury, Reuter, Christian, Mitzel, Norbert W., and Della Vedova, Carlos O. “The Structure and Conformation of (CH3)(3)CSNO”. Chemistry - A European Journal 21.29 (2015): 10436-10442.

2 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Computational Structural Biology of S-nitrosylation of Cancer Targets.
Bignon E, Allega MF, Lucchetta M, Tiberti M, Papaleo E., Front Oncol 8(), 2018
PMID: 30155439

37 References

Daten bereitgestellt von Europe PubMed Central.

S-nitrosylation of proteins with nitric oxide: synthesis and characterization of biologically active compounds.
Stamler JS, Simon DI, Osborne JA, Mullins ME, Jaraki O, Michel T, Singel DJ, Loscalzo J., Proc. Natl. Acad. Sci. U.S.A. 89(1), 1992
PMID: 1346070

Oae, Org. Prep. Proced. 15(), 1983

Levett, Sci. Rep. 109(), 2011

Greenwald, PLoS ONE 5(), 2010
Nitrosothiol esters of diclofenac: synthesis and pharmacological characterization as gastrointestinal-sparing prodrugs.
Bandarage UK, Chen L, Fang X, Garvey DS, Glavin A, Janero DR, Letts LG, Mercer GJ, Saha JK, Schroeder JD, Shumway MJ, Tam SW., J. Med. Chem. 43(21), 2000
PMID: 11052806
On the role of the simplest S-nitrosothiol, HSNO, in atmospheric and biological processes.
Hochlaf M, Linguerri R, Francisco JS., J Chem Phys 139(23), 2013
PMID: 24359364
Sulfur K-edge X-ray absorption spectroscopy as an experimental probe for S-nitroso proteins.
Szilagyi RK, Schwab DE., Biochem. Biophys. Res. Commun. 330(1), 2005
PMID: 15781232

Romano, J. Mol. Struct. 522(), 2000

Carnahan, Acta Crystallogr. B 34(), 1978

Arulsamy, J. Am. Chem. Soc. 121(), 1999

Bartberger, J. Am. Chem. Soc. 122(), 2000
A surprisingly stable S-nitrosothiol complex.
Perissinotti LL, Estrin DA, Leitus G, Doctorovich F., J. Am. Chem. Soc. 128(8), 2006
PMID: 16492016
Modulating nitric oxide release by S-nitrosothiol photocleavage: mechanism and substituent effects.
Marazzi M, Lopez-Delgado A, Fernandez-Gonzalez MA, Castano O, Frutos LM, Temprado M., J Phys Chem A 116(26), 2012
PMID: 22667985

Mason, J. Chem. Soc. A (), 1969

Romano, J. Mol. Struct. 513(), 1999
NO affinities of s-nitrosothiols: a direct experimental and computational investigation of RS-NO bond dissociation energies.
Lu JM, Wittbrodt JM, Wang K, Wen Z, Schlegel HB, Wang PG, Cheng JP., J. Am. Chem. Soc. 123(12), 2001
PMID: 11456986
Resonance description of S-nitrosothiols: insights into reactivity.
Timerghazin QK, Peslherbe GH, English AM., Org. Lett. 9(16), 2007
PMID: 17616141

Timerghazin, Chem. Phys. Lett. 454(), 2008
Conformational properties of ethyl- and 2,2,2-trifluoroethyl thionitrites, (CX₃CH₂SNO, X = H and F).
Canneva A, Della Vedova CO, Mitzel NW, Erben MF., J Phys Chem A 119(9), 2014
PMID: 25188900

Philippe, Spectrochim. Acta 17(), 1961

Fu, J. Phys. Chem. A 106(), 2002

Field, J. Chem. Soc. Chem. Commun. (), 1978

Lee, Can. J. Chem. 79(), 2001

Goto, Tetrahedron Lett. 41(), 2000

Della, Inorg. Chem. 32(), 1993

AUTHOR UNKNOWN, 0
The decomposition of thionitrites.
Stamler JS, Toone EJ., Curr Opin Chem Biol 6(6), 2002
PMID: 12470731

Christensen, Spectrochim. Acta A 24(), 1968

Tasker, J. Chem. Soc. 95(), 1909

Berger, Z. Naturforsch. B 64(), 2009

AUTHOR UNKNOWN, 0

Vishnevskiy, J. Mol. Struct. 833(), 2007

Vishnevskiy, J. Mol. Struct. 871(), 2007

AUTHOR UNKNOWN, 0

Perutz, J. Chem. Soc. Faraday Trans. 2 69(), 1973

Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®

Quellen

PMID: 26095109
PubMed | Europe PMC

Suchen in

Google Scholar