Thione-thiol tautomerism and stability of 2- and 4-mercaptopyridines and 2-mercaptopyrimidines

Full text of DOI:10.1139/v90-227

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. E. A. Ramírez, E. Cortés, A. A. Rubert, P. Carro, G. Benítez, M. E. Vela, R. C. Salvarezza. 2012. Complex Surface Chemistry
of 4-Mercaptopyridine Self-Assembled Monolayers on Au(111). Langmuir 120419165241009. [CrossRef]
. Nazly Hassan, Rudolf Holze. 2012. Surface enhanced Raman spectroscopy of self-assembled monolayers of 2-mercaptopyridine
on a gold electrode. Russian Journal of Electrochemistry 48:4, 401-411. [CrossRef]
. Y. Kotaiah, N. Hari Krishna, K. Naga Raju, C.V. Rao, S.B. Jonnalagadda, Suresh Maddila. 2012. Synthesis and Biological
Evaluation of Novel Isopropyl 2-thiazolopyrimidine-6-carboxylate Derivatives. Journal of the Korean Chemical Society 56:1, 68-73.
[CrossRef]
4
5
6
. Saleh Shakhatreh, Maria Lalia-Kantouri, Maria Gdaniec, Pericles D. Akrivos. 2012. Study of copper(I) heteroleptic compounds
with 1-phenyl-1, 4-dihydro-tetrazole-5-thione and triphenylphosphine. Journal of Coordination Chemistry 65:2, 251-261.
[
CrossRef]
. Suresh Maddila, Sreekantha B. Jonnalagadda. 2012. Synthesis and Biological Activity of Ethyl 2-(substituted benzylthio)-4-
3′-(ethoxycarbonyl)biphenyl-4-yl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate Derivatives. Archiv der Pharmazie 345:2, 163.
CrossRef]
. Rui Du, Chong Liu, Yanying Zhao, Ke-Mei Pei, Hui-Gang Wang, Xuming Zheng, Mingde Li, Jia-Dan Xue, David Lee Phillips.
011. Resonance Raman Spectroscopic and Theoretical Investigation of the Excited State Proton Transfer Reaction Dynamics
(
[
2
of 2-Thiopyridone. The Journal of Physical Chemistry B 115:25, 8266-8277. [CrossRef]
7
8
. References 587-673. [CrossRef]
. Mosaad S. Mohamed, Rehab Kamel, Samar S. Fatahala. 2010. Synthesis and biological evaluation of some thio containing pyrrolo
[2,3-d]Pyrimidine derivatives for their anti-inflammatory and anti-microbial activities. European Journal of Medicinal Chemistry
45:7, 2994. [CrossRef]
9. Edwin C. Constable, Catherine E. Housecroft, Markus Neuburger, Jason R. Price, Jennifer A. Zampese. 2010. Tuning
Coordination Environments Through Ligand Redox Chemistry: the Thiol–Disulfide Reaction. Australian Journal of Chemistry
63:9, 1334. [CrossRef]
10. Norman P. Schepp, Christopher J. M. Green, Frances L. Cozens. 2010. Non-resonant two-photon photochemistry of a Barton
ester, N-phenylacetyloxy-2-pyridinethione. Photochemical & Photobiological Sciences 9:1, 110. [CrossRef]
11. M. T. Molina, M. Yáñez, O. Mó, R. Notario, J.-L. M. AbboudThe Thiocarbonyl Group . [CrossRef]
12. Mohamed A. A. Radwan, Eman M. H. Abbas. 2009. Synthesis of some pyridine, thiopyrimidine, and isoxazoline derivatives based
on the pyrrole moiety. Monatshefte für Chemie - Chemical Monthly 140:2, 229-233. [CrossRef]
1
3. Sin Yee Ng, Weng Kee Leong, Lai Yoong Goh, Richard D. Webster. 2008. Synthesis, X-ray Crystal Structures and
Electrochemistry of (Indenyl)ruthenium Complexes Containing dppf and Heterocyclic Thiolato/Thione Ligands. European
Journal of Inorganic Chemistry 2008:1, 144-151. [CrossRef]
1
1
1
4. Claudio C. Silveira, Samuel R. Mendes. 2007. Catalytic oxidation of thiols to disulfides using iodine and CeCl3·7H2O in graphite.
Tetrahedron Letters 48:42, 7469-7471. [CrossRef]
5. Salomé Delgado, Agustín Molina-Ontoria, Manuela E. Medina, Cesar J. Pastor, Reyes Jiménez-Aparicio, José L. Priego. 2007.
Structural diversity of copper complexes with angular and linear dipyridyl ligands. Polyhedron 26:12, 2817-2828. [CrossRef]
6. L PINHEIRO, M TEMPERINI. 2007. Pyridine and pyridine carboxylic acids as guests in a bidimensional hydrogen bond
structure analyzed by scanning tunneling microscopy. Surface Science 601:8, 1836-1843. [CrossRef]
17. Branko Stanovnik, Miha Tišler, Alan R. Katritzky, Olga V. Denisko 91, 1. [CrossRef]
18. Rajendra N. Goyal, Sham M. Sondhi, Anand M. Lahoti. 2006. Electrochemical Investigations of Biologically Active 1-
(3-Hydroxy-2-pyridyl)-4,4,6-trimethyl-3,4-dihydropyrimidine-2[1H]-thione at Pyrolytic Graphite Electrode. Bulletin of the
Chemical Society of Japan 79:4, 569-576. [CrossRef]
1
9. Andreas Eichhöfer, Gernot Buth. 2005. Synthesis and Structure of the Group 12 Pyrimidinethiolate Complexes∞3[Zn(S-2-
N2C4H3)2],∞2[Cd(S-2-N2C4H3)2], [Hg(S-2-N2C4H3)2] and[Cd(S-2-N2C4H3)2(tmeda)]. European Journal of Inorganic
Chemistry 2005:20, 4160-4167. [CrossRef]
20. Josefa Ángela García Calzón, Jesús Luis Muñiz Álvarez, Juan Miguel López Fonseca. 2005. Oxidation process induced by 2-
mercaptopyrimidine at a mercury electrode. Journal of Colloid and Interface Science 290:2, 498-504. [CrossRef]
2
1. Mitra Ghassemzadeh, Forough Adhami, Abas Taeb, Majid M. Heravi, Bernhard Neumüller. 2005. A Coordination Polymer
from HAMTTO with Silver(I) (HAMTTO = 4-Amino-6-methyl-1,2,4-triazine-3-thione-5-one). Zeitschrift für anorganische
und allgemeine Chemie 631:9, 1568-1570. [CrossRef]

22. Sham M. Sondhi, Rajendra N. Goyal, Anand M. Lahoti, Nirupma Singh, Rakesh Shukla, Ram Raghubir. 2005. Synthesis and
biological evaluation of 2-thiopyrimidine derivatives. Bioorganic & Medicinal Chemistry 13:9, 3185-3195. [CrossRef]
23. Edwin C. Constable, B. A. Hermann, Catherine E. Housecroft, Markus Neuburger, Silvia Schaffner, Lukas J. Scherer. 2005.
2
,2′:6′,2″-Terpyridine-4′(1′H)-thione: a missing link in metallosupramolecular chemistry. New Journal of Chemistry 29:11, 1475.
CrossRef]
4. Sebastian Muthu, Jagadese J. Vittal. 2004. A New Polymorph of 4-Pyridinethione Containing a Helical Assembly Based on N
H···S Hydrogen Bonds. Crystal Growth & Design 4:6, 1181-1184. [CrossRef]
[
2
2
2
−
5. H. Hanika-Heidl, R.D. Fischer. 2004. Versatile reaction of the potential host system [(Me3SnIV) 4RuII(CN) 6]∞ with 4-
thiopyridone/4-mercaptopyridine in water. Inorganica Chimica Acta 357:6, 1748-1760. [CrossRef]
6. Jaros?aw Spycha?a. 2003. Correlation between the reactivity and spectroscopic properties ofN-substituted secondary thioamides.
New intramolecular N���H+���N binding approach and proton complexes based on thioamide ligation. Magnetic Resonance in
Chemistry 41:3, 169-176. [CrossRef]
27. R FERNANDES. 2002. Organotin(IV) complexes of 4,6-dimethylpyrimidine-2-thione, Me2PymtH. Preparation,
characterization and crystal structure determination of cis-6Ph2Sn(Me2Pymt)29 and 6Ph3Sn(Me2Pymt)9. Polyhedron 21:12-13,
1149-1153. [CrossRef]
28. Maged A. El-Kemary, Mohamed E. El-Khouly, Osamu Ito. 2000. Photophysical characteristics of two 4,6-disubistituted-3-
cyanopyridin-2(1H)-thiones in various solvents. Journal of Photochemistry and Photobiology A: Chemistry 137:2-3, 105-113.
[CrossRef]
2
3
3
3
3
3
3
3
9. L Pinheiro. 1999. Coadsorption of 2-mercaptopyrimidine and 2,2′-bipyridine on Au(111) studied by scanning tunneling
microscopy. Surface Science 441:1, 45-52. [CrossRef]
0. L Pinheiro. 1999. Coadsorption of 2-mercaptopyrimidine and 1,10′-phenanthroline on Au(111) as seen by STM. Surface Science
441:1, 53-64. [CrossRef]
1. A Demir. 1999. Novel conversion of thiols into disulfides, via S-nitrosothiol intermediates using trichloronitromethane.
Tetrahedron 55:42, 12399-12404. [CrossRef]
2. L Herczynska. 1999. Modification of polysiloxanes by free-radical addition of pyridylthiols to the vinyl groups of the polymer.
European Polymer Journal 35:6, 1115-1122. [CrossRef]
3. C TAVAGNACCO, S PERESSINI, G COSTA, M BORSARI, R BATTISTUZZI. 1998. Electrochemistry of 2-thio- and 2-
oxo-pyrimidines in dimethyl formamide in the presence of dioxygen. Inorganica Chimica Acta 270:1-2, 145-150. [CrossRef]
4. Eric S. Raper. 1997. Complexes of heterocyclic thionates Part 2: complexes of bridging ligands. Coordination Chemistry Reviews
165, 475-567. [CrossRef]
5. S. Stoyanov, T. Stoyanova, L. Antonov, P. Karagiannidis, P. Akrivos. 1996. Thione-disulfide interchange of some heterocyclic
tautomeric thiones and their symmetrical disulfides. Monatshefte für Chemie - Chemical Monthly 127:5, 495-504. [CrossRef]
6. Stefan Stoyanov, Tatyana Stoyanova, Pericles D. Akrivos, Petros Karagiannidis, Peter Nikolov. 1996. Spectroscopic and
computational investigation of the ground and low excited states of some symmetrical heterocyclic disulfides. Journal of Heterocyclic
Chemistry 33:3, 927-931. [CrossRef]
3
3
3
4
7. M. D. Couce, V. Cherchi, G. Faraglia, U. Russo, L. Sindellari, G. Valle, N. Zancan. 1996. Synthesis and characterization of
organotin complexes with 2-mercaptopyridine derivatives. Applied Organometallic Chemistry 10:1, 35-45. [CrossRef]
8. M.D Couce, G Faraglia, U Russo, L Sindellari, G Valle. 1996. Synthesis, characterisation and X-ray crystal structures of
diorganotin(IV) complexes with 2-mercaptopyridine derivatives. Journal of Organometallic Chemistry 513:1-2, 77. [CrossRef]
9. J Contreras. 1995. Ab initio SCRF study of the tautomeric equilibrium of 2-thiopyrimidine. Chemical Physics Letters 232:1-2,
61-66. [CrossRef]
0. Krzysztof J. Reszka, Colin F. Chignell. 1994. PHOTOCHEMISTRY OF 2-MERCAPTOPYRIDINES. PART 1. AN EPR
AND SPIN-TRAPPING INVESTIGATION USING 5,5-DIMETHYLl-PYRROLINE N-OXIDE IN AQUEOUS AND
TOLUENE SOLUTIONS. Photochemistry and Photobiology 60:5, 442-449. [CrossRef]
4
4
4
1. J.Guillermo Contreras, Gloria V. Seguel, Joel B. Alderete. 1994. The vibrational spectra of some 2-mercaptopyrimidine complexes
of mercury(II). Spectrochimica Acta Part A: Molecular Spectroscopy 50:2, 371-374. [CrossRef]
2. Eric S. Raper. 1994. Copper complexes of heterocyclic thioamides and related ligands. Coordination Chemistry Reviews 129:1-2,
91-156. [CrossRef]
3. Margaret C. Etter, John C. MacDonald, Randall A. Wanke. 1992. Solution and solid-state aggregation properties of 4-
mercaptopyridine-4-thiopyridone. Journal of Physical Organic Chemistry 5:4, 191-200. [CrossRef]

44. Jörg Breitenbach, Martin Nieger, Fritz Vögtle. 1991. 7,15-Dihydroxy[2.2](2,6)pyridinophan: Darstellung über selenoorganische
Stufen und Aggregation durch Wasserstoff-Brückenbindungen. Chemische Berichte 124:11, 2583-2586. [CrossRef]
45. S. STOYANOV, I. PETKOV, L. ANTONOV, T. STOYANOVA, P. KARAGIANNIDIS, P. ASLANIDIS. 1991. ChemInform
Abstract: Thione-Thiol Tautomerism and Stability of 2- and 4-Mercaptopyridines and 2-Mercaptopyrimidines. ChemInform
22:8, no-no. [CrossRef]