Температурные зависимости давления насыщенного пара комплексов олова(IV) с полидентатными лигандами

N. M. Lazarev; B. I. Petrov; A. V. Piskunov; T. S. Pochekutova; V. V. Semenov

Authors

N. M. Lazarev G.A. Razuvaev Institute of Organometallic Chemistry of the RAS
B. I. Petrov G.A. Razuvaev Institute of Organometallic Chemistry of the RAS
A. V. Piskunov G.A. Razuvaev Institute of Organometallic Chemistry of the RAS
T. S. Pochekutova G.A. Razuvaev Institute of Organometallic Chemistry of the RAS
V. V. Semenov G.A. Razuvaev Institute of Organometallic Chemistry of the RAS

Keywords:

tin(IV) organometallic complexes, Schiff bases, DSC, Knudsen effusion method, phase transition, vapor pressure, thermodynamic parameters of sublimation

Abstract

The present paper is a continuation of the previously pursued studies of thermal properties of the Sn(IV) complexes with tridentate iminopyridine ligands. The study of thermal properties including temperature dependences of the saturated vapor pressure for Sn(IV) complexes with the tridentate iminopyridine ligands by differential scanning calorimetry (DSC) and the Knudsen effusion method leads to the use of the studied compounds as luminescent materials, as well as components for nonlinear optics. Coordination compounds of tin (IV) containing tridentate Schiff bases were chosen as objects of research: 2,4-di-tert-butyl-6-((phenyl (pyridin-2-yl)methylene)amino)phenolatotrichlorotin(IV) (1), 4-methyl-2-((phenyl (pyridin-2-yl)methylene)amino)phenolatotrichlorotin(IV) (2), 4-chloro-2-((phenyl (pyridin-2-yl)methylene)amino) phenolatotrichlorotin(IV) (3). These compounds were obtained by template synthesis from tin tetrachloride, various o-aminophenols, and α-carbonyl substituted pyridines; they contain an iminopyridine function and are capable of covalently binding to a metal by a phenolic group. Phase transitions of compounds 1–3 were studied by DSC in the temperature range 25–500 °C. For all studied complexes an endothermic transition correlated to melting was revealed. The melting points of the studied compounds were taken to be the temperature values corresponding to the onset of the transition, according to the standard Netzsch Software Proteus method: 300, 320 and 330 °C for 1–3, respectively. The temperature dependences of the saturated vapor pressure were obtained for the studied complexes, using the Knudsen effusion method with the weight recording of the amounts of sublimated substances. As a result of the experiments it was found that compounds 1–3 sublimated in the temperature ranges of 239–244, 228–260 and 226–256 °C, respectively. Thermodynamic parameters of sublimation processes were calculated.

Author Biographies

N. M. Lazarev, G.A. Razuvaev Institute of Organometallic Chemistry of the RAS

кандидат химических наук, научный сотрудник

B. I. Petrov, G.A. Razuvaev Institute of Organometallic Chemistry of the RAS

доктор технических наук, ведущий научный сотрудник, заместитель директора

A. V. Piskunov, G.A. Razuvaev Institute of Organometallic Chemistry of the RAS

доктор химических наук, профессор РАН, заместитель директора

T. S. Pochekutova, G.A. Razuvaev Institute of Organometallic Chemistry of the RAS

научный сотрудник

V. V. Semenov, G.A. Razuvaev Institute of Organometallic Chemistry of the RAS

доктор химических наук, ведущий научный сотрудник

References

Dhar, D.N. Schiff Bases and Their Applications / D.N. Dhar, C.L. Taploo // J. Sci. Ind. Res. (In-dia). – 1982. – V. 41, iss. 8. – P. 501–506.

Schiff Bases: a Versatile Pharmacophore / A. Kajal, S. Bala, S. Kamboj et al. // J. Catal. – 2013. – V. 2013. – P. 1–15. DOI: 10.1155/2013/893512.

Metal Complexes Driven from Schiff Bases and Semicarbazones for Biomedical and Allied Applications: a Review / M.S. More, P.G. Joshi, Y.K. Mishra et al. // Mater. Today Chem. – 2019. – V. 14. – 100195. DOI: 10.1016/j.mtchem.2019.100195.

Application of Metal Complexes of Schiff Bases-a Review / S. Kumar, D. Nath Dhar, P.N. Saxena et al. // J. Sci. Ind. Res. (India). – 2009. – V. 68, iss. 3. – P. 181–187.

. Synthesis, Characterization and Anti-inflammatory Evaluation of New Fluorobenzothiazole Schiff's Bases / B.S. Sathe, E. Jaychandran, V.A. Jagtap et al. // Int. J. Curr. Pharm. Res. – 2011. – V. 3, iss. 3. – P. 164–169.

A Systemic Review of Schiff Bases as an Analgesic, Anti-inflammatory / K.Rana, A. Pandurangan, N. Singh et al. // Int. J. Curr. Pharm. Res. – 2011. – V. 4, iss. 2. – P. 5–11.

Synthesis of Schiff Bases of 2-Amino-5-aryl-1,3,4-thiadiazole and its Analgesic, Anti-Inflammatory, Anti-Bacterial and Anti-Tubercular Activity / A. Pandey, D. Dewangan, S. Verma et al. // Int. J. Chemtech. Res. – 2011. – V. 3, iss. 1. – P. 178–184. DOI: 10.1155/2012/145028.

Synthesis and Biological Screening of Certain New Triazole Schiff Bases and Their Derivatives Bearing Substituted Benzothiazole Moiety / C. Chandramouli, M.R. Shivanand, T.B. Nayanbhai et al. // J. Chem. Pharm. – 2012. – V. 4, iss. 2. – P. 1151–1159.

Synthesis and Biological Evaluation of Schiff Bases of 4-Iminophenazone as an Anti-inflammatory, Analgesic and Antipyretic Agent / S. Murtaza, M.S. Akhtar, F. Kanwal et al. // J. Saudi Chem. Soc. – 2017. –V. 21, iss. 1. – P. 359–372.

Antimicrobial Activity Studies of Mononuclear and Binuclear Mixed-Ligand Copper(II) Com-plexes Derived from Schiff Base Ligands and 1,10-Phenathroline / M. Tumer, H. Koksal, S. Serin et al. // Transit. Met. Chem. – 1999. – V. 24. – P. 13–17. DOI: 10.1023/A:1006996722406.

Schiff Bases: a Short Review of Their Antimicrobial Activities / C.M. das Silva, D.L. da Silva, L.V. Modolo et al. // J. Adv. Res. – 2011. – V. 2, Iss. 1. – P. 1–8. DOI: 10.1016/j.jare.2010.05.004

Synthesis and Antimicrobial Activities of Schiff Bases Derived from 5-Chloro-salicylaldehyde / L. Shi, H.-M. Ge, S.-H. Tan et al. // Eur. J. Med. Chem. – 2007. – V. 42, iss. 4. – P. 558–564. DOI: 10.1016/j.ejmech.2006.11.010

Synthesis of Schiff Bases of 4-(4-Aminophenyl)-morpholine as Potential Antimicrobial Agents / P. Panneerselvam, R,R, Nair, G. Vijayalakshmi et al. // Eur. J. Med. Chem. – 2005. – V. 40, iss. 2. – P. 225–229. DOI: 10.1016/j.ejmech.2004.09.003.

Ispir, E. Synthesis, Characterization, Antimicrobial and Genotoxic Activities of New Schiff Ba-ses and Their Complexes / E. Ispir, S. Toroglu, A. Kayraldiz // Transit. Metal Chem. – 2008. – V. 33, iss. 8. – P. 953–960. DOI: 10.1007/s11243-008-9135-2.

Antibacterial, Antifungal and in vitro Antileukaemia Activity of Metal Complexes with

Thiosemicarbazones / E. Pahonty, F. Julea, T. Rosu et al. // J. Cell. Mol. Med. – 2015. – V. 19, iss. 4. – P. 865–878. DOI: 10.1111/jcmm.12508.

Characteristic Spectral Studies and in vitro Antifungal Activity of Some Schiff Bases and Their Organotin(IV) Complexes / W. Rehman, M.K. Baloch, B. Muhammad et al. // Chi. Sci. Bull. – 2004. – V. 49. – P. 119–122. DOI: 10.1360/03wb0174.

Schiff Bases as Potential Fungicides and Nitrification Inhibitors / N. Aggarwal, R. Kumar, P. Dureja et al. // J. Agric. Food Chem. – 2009. – V. 57, Iss. 18. – P. 8520–8525. DOI: 10.1021/jf902035w

Chaubey, A. N. Synthesis and Anticonvulsant Activity (Chemo Shock) of Schiff and Mannich Bases of Isatin Derivatives with 2-amino Pyridine (Mechanism of Action) / A.N. Chaubey S.N. Pandeya // Int. J. Pharmtech. Res. – 2012. – V. 4, iss. 4. – P. 590–598. DOI: 10.11648/j.ajhc.20190502.12

Hearn, M. J. Design and Synthesis of Antituberculars: Preparation and Evaluation Against My-cobacterium Tuberculosis of an Isoniazid Schiff Base / M.J. Hearn, M.H. Cynamon // J. Antimocrob. Chem. – 2004. – V. 53, iss. 2. – P. 185–191. DOI: 10.1093/jac/dkh041.

Aboul-Fadl, T. Synthesis, Antitubercular Activity and Pharmacokinetic Atudies of some Schiff Bases Derived from 1-Alkylisatin and Isoicotinic Acid Hydrazide (INH) / T. Aboul-Fadl, F.A. Moham-med, E.A. Hassan // Arch. Pharm. Res. – 2003. – V. 26, iss. 10. – P. 778–784. DOI: 10.1007/BF02980020

Recent Advances in Iron Complexes as Potential Anticancer Agents / W.A. Wani, U. Baig, S. Shreaz et al. // New J. Chem. – 2016. – V. 40, iss. 2. – P. 1063–1090. DOI: 10.1039/C5NJ01449B.

Sridevi, G. Schiff Bases Metal Complexes as Anticancer Agents / G. Sridevi, S. A. Antony, R. Angayarkani // Asian J. Chem. – 2019. – V. 31, iss. 3. – P. 493–504. DOI: 10.14233/ajchem.2019.21697

Tadele, K.T. Schiff Bases and Their Metal Complexes as Potential Anticancer Candidates: a Review of Recent Works / K.T. Tadele, T.W. Tsega // AntiCancer Agents Med. Chem.. – 2019. – V. 19, iss. 15. – P. 1786–1795. DOI: 10.2174/18715206196661902271716.

Miri, R. QM Study and Conformational Analysis of am Isatin Schiff Base as a Potentional Cytoxic Agent / R. Miri, N. Razzaghi-asl, M.K. Mohammadi // J. Mol. Mod. – 2013. – V. 19. – P. 727–735. DOI: 10.1007/s00894-012-1586-x.

The Role of Aromatic Schiff Bases in the Dyes Techniques / K.M. Abuamer, A.A. Maihub, M.M. El-Ajaily et al. // Inter. J. Organic. Chem. – 2014. – V. 4, iss. 1. – P. 7–15. DOI: 10.4236/ijoc,2014.41002.

Visual-Pigment Spectra: Implications of the Protonation of the Retinal Schiff Base / B. Honig, A. D. Greenberg, U. Dinur et al. // Biochem. – 1976. – V. 15, iss. 21. – P. 4593–4599. DOI: 10.1021/bi00666a008.

A Highly Sensitive and Selective Fluorescent Sensor for the Determination of Copper(II) Based on a Schiff Base. // N Aksuner, E Henden, I Yilmaz et al. // Dyes Pigm. – 2009. – V. 83, iss. 2. – P. 211–217. DOI: 10.1016/j.dyepig.2009.04.012.

Tanaka, K. Synthesis, Crystal Structures and Photochromic Properties of Novel Chiral Schiff Base Macrocycles / K. Tanaka, R. Shimoura, M.R. Caira // Tetrahedron Lett. – 2010. – V. 51, Iss. 2. – P. 449–452. DOI: 10.1016/j.tetlet.2009.11.062.

Investigation on Some Schiff Bases as HCl Corrosion Inhibitors for Copper/ S. Li, S. Chen., S. Lei et al. // Corros. Sci. – 1999. – V. 41, iss. 7. – P. 1273–1287. DOI: 10.1016/S0010-938X(98)00183 8.

Blue Electroluminescence in Thin Films of Azomethin-zinc Complexes / Y. Hamada, T. Sano, M. Fujita et al. // Jpn. J. Appl. Phys. – 1993. – V. 32, iss. 4. – P. L511–L513. DOI: 10.1143/JJAP.32.L511.

Synthesis, Crystal Structure and Photoluminescence Study of Green Light Emitting bis(1[4-butylphenyl)imino]methyl haphthalen-2-ol) Ni (II) Complex / M. Srinivas, T.O. Shrungesh Kumar, K.M. Mahadevan et al. // J. Science: Adv. Mater. and Devices. – 2016. – V. 1. – P. 324–329. DOI: 10.1016/j.samd.2016.07.002.

Coordination of N,O-donor Appended Schiff Base Ligand (H2L1) towards Zinc(II) in Presence of Pseudohalides: Syntheses, Crystal Structures, Photoluminescence, Antimicrobial Activities and Hirshfeld Surfaces / D. Majumdar, J.K. Biswas, M. Mondal et al. // J. Mol. Struct. – 2018. – V. 1155. – P. 745–757. DOI: 10.1016/j.molstruc.2017.11.052.

Температурные зависимости давления насыщенного пара комплексов олова(IV) с триден-татными иминопиридиновыми лигандами / Б.И. Петров, А.В. Пискунов, О.Ю. Трофимова и др. // Вестник ЮУрГУ. Серия «Химия». – 2020. – Т. 12, № 3. – С. 116–124. DOI: 10.14529/chem200307.

Темплатный синтез комплексов олова(IV) с тридентатными иминоприридиновыми ли-гандами / А.В. Пискунов, О.Ю. Трофимова, А.В. Малеева, А.В. Черкасов // Координационная химия. – 2019. – Т. 45, № 3. – С. 158–169. DOI: 10.1134/S0132344X1902004X

Hohne, G. W. H. Differential Scanning Calorimetry / G.W.H. Hohne, W.F. Hemminger, H.F. Flammersheim. – Berlin; Heidelberg: Springer-Verlag, 2003. – 299 p.

Drebushchak, V.A. Calibration Coefficient of a Heat-flow DSC. Part II. Optimal Calibration Procedure / V.A. Drebushchak // J. of Therm. and Cal. – 2005. – V. 79, № 1. – P. 213–218. DOI: 10.1007/s10973-004-0586-1

Knudsen, M. Die Molekularstromung der Gase Durch Offnungen und die Effusion / M. Knud-sen. – 1909. – V. 333, № 5. – P. 999–1016. DOI: 10.1002/andp.19093330505

Лебедев, Ю.А. Термохимия парообразования органических веществ / Ю.А. Лебедев, Е.А. Мирошниченко. – М.: Наука, 1981. – 216 с.

Сыркин В.Г. Карбонилы металлов / В.Г. Сыркин. – М.: Наука, 1983. – 200 с.