Synthesis and Structure Investigation of Organic Compounds of Antimony (V) with Unsaturated Carbonic Acids Ph3Sb[OC(O)R]2

Authors

  • A. I. Maleeva Lobachevsky State University of Nizhni Novgorod, Nizhny Novgorod, Russian Federation
  • A. V. Gushchin Lobachevsky State University of Nizhni Novgorod, Nizhny Novgorod, Russian Federation
  • O. S. Kalistratova Lobachevsky State University of Nizhni Novgorod, Nizhny Novgorod, Russian Federation
  • P. V. Andreev Lobachevsky State University of Nizhni Novgorod, Nizhny Novgorod, Russian Federation
  • N. V. Somov Lobachevsky State University of Nizhni Novgorod, Nizhny Novgorod, Russian Federation

Keywords:

crystalline structure, triphenylantimony, triphenylantimony diacrylate, triphenylantimony dimethacrylate, triphenylantimony dicrotonate, triphenylantimony bisphurylacrylate, triphenylantimony dicinnamate, triphenylantimony di-meta-nitrocinnamate

Abstract

Triphenylantimony dicarboxylates Ph3Sb[OC(O)CH=CH2]2, Ph3Sb[OC(O)C(CH3)=CH2]2, Ph3Sb[OC(O)CH=CHCH3]2, Ph3Sb[OC(O)CH=CHC4H3O]2, Ph3Sb[OC(O)CH=CHPh]2, Ph3Sb[OC(O)CH=CHC6H4NO2-m]2, Ph3Sb[OC(O)CH=CHC6H4OMe-p]2, Ph3Sb[OC(O)CH=CHCH=CHCH3]2 were obtained with the reaction of triphenylantimony and carboxylic acids in the presence of hydrogen peroxides in ether or THF. Triphenylantimony dicarboxylate yields were 59–86 %. The structure of the obtained products was confirmed by elemental analysis, IR, 1H-NMR spectroscopy. According to the X-ray diffraction data, the antimony atom can be in a trigonal-bipyramidal, tetragonal-pyramidal, and “intermediate” configuration. In all compounds additional coordination of the antimony atom with carbonyl oxygen atoms is observed, and this effect is most pronounced in triphenylantimony m-nitrocinnamate. In the case of a distorted trigonal-bipyramidal configuration, the two angles in the equatorial plane vary within 104,03(4)–112,59(9), the third angle significantly exceeds these values 135,43(9)–149,81(8). This fact is associated with the location of carbonyl oxygen atoms O2 and O4 between the phenyl substituents. The sum of the angles in the equatorial plane is 360º. Ranges of the Sb–O and Sb–C bond lengths are 2,104(2)–2,163(7) Å and 2,103(16)–2,128(1) Å. The O1–Sb–O3 bond angles are 172,18 (6)–78,00 (4)º. The intramolecular Sb…O2 and Sb…O4 distances are equal to 2,583–3,060 Å. The carboxylate residue of unsaturated carboxylic acids has a flat structure, all valent angles are close to 120º, which confirms the participation of all carbon and oxygen atoms in the formation of the single conjugate C=C–C(O)OSb system. In this case multiple bonds are shortened, while single bonds are elongated compared to those in acids. Intermolecular interactions in triphenylantimony acrylate, methacrylate, crotonate, and sorbate with the C=C double bonds of unsaturated carboxylate fragments of neighboring molecules have been revealed. In some compounds there is a co-crystallized solvent, which is included in the molecular packing.

Author Biographies

A. I. Maleeva, Lobachevsky State University of Nizhni Novgorod, Nizhny Novgorod, Russian Federation

аспирант химического факультета

A. V. Gushchin, Lobachevsky State University of Nizhni Novgorod, Nizhny Novgorod, Russian Federation

доктор химических наук, профессор кафедры органической химии

O. S. Kalistratova, Lobachevsky State University of Nizhni Novgorod, Nizhny Novgorod, Russian Federation

аспирант химического факультета

P. V. Andreev, Lobachevsky State University of Nizhni Novgorod, Nizhny Novgorod, Russian Federation

кандидат физико-математических наук, м.н.с., ассистент кафедры кристаллографии и экспериментальной физики физического факультета

N. V. Somov, Lobachevsky State University of Nizhni Novgorod, Nizhny Novgorod, Russian Federation

кандидат физико-математических наук, доцент кафедры кристаллографии и экспериментальной физики физического факультета

References

Шарутин, В.В. Строение органических соединений сурьмы(V) R3SbX2 (X – электро-отрицательный лиганд) / В.В. Шарутин, О.К. Шарутина // Бутлеровские сообщения. – 2007. – Т. 12, № 6. – С. 34–57.

Молекулярные и кристаллические структуры карбоксилатов три- и тетраарилсурьмы / В.В. Шарутин, В.С. Сенчурин, О.К. Шарутина, О.В. Чагарова // Вестник ЮУрГУ. Серия «Химия». – 2011. – Вып. 6. – С. 47–60.

Synthesis, Structural Characterization and in vitro Antitumour Properties of Triorganoantimony(V) Disalicylates: Crystal and Molecular Structures of [5-Y-2-(ho)-C6H3COO]2SbMe3 (Y = H, Me, MeO) / C. Silvestru, I. Haiduc, R.T. Tiekink et al. // Appl. Organomet. Chem. – 1995. – V. 9, № 7. – P. 597–607. DOI: 10.1002/aoc.590090715.

Synthesis, Characterization and in vitro Antitumor Activity of Some Arylantimony Ferrocenecarboxylates and Crystal Structures of C5H5FeC5H4CO2SbPh4 and (C5H5FeC5H4CO2)2Sb(4-CH3C6H4)3 / R.C. Liu, Y.Q. Ma, L. Yu et al. // Appl. Organomet. Chem. – 2003. – V. 17, № 9. – P. 662–668. DOI: 10.1002/aoc.491.

Synthesis, Crystal Structures and in vitro Antitumor Activities of Some Arylantimony Derivatives of Analogues of Demethylcantharimide / G.C. Wang, J. Xiao, L. Yu et al. // J. Organomet. Chem. – 2004. – V. 689, № 9. – P. 1631–1638. DOI: 10.1016/j.jorganchem.2004.02.015.

Mishra, J. Chemotherapy of Leishmaniasis: Past, Present and Future / J. Mishra, A. Saxena, S. Singh // Curr. Med. Chem. – 2007. – V. 14, № 10. – P. 1153–1169. DOI: 10.2174/092986707780362862.

Novel Triphenylantimony(V) and Triphenylbismuth(V) Complexes with Benzoic Acid Derivatives: Structural Characterization, in vitro Antileishmanial and Antibacterial Activities and Cytotoxicity against Macrophages / A. Islam, J.G. Da Silva, F.M. Berbet et al. // Molecules. – 2014. – V. 19, № 5. – P. 6009–6030. DOI:10.3390/molecules19056009.

Anti-leishmanial Activity of Heteroleptic Organometallic Sb(V) Compounds / M.I. Ali, M.K. Rauf, A. Badshah et al. // Dalton Trans. – 2013. – V. 42, № 48. – P. 16733–16741. DOI: 10.1039/c3dt51382c.

High-Sensitivity Molecular Organometallic Resist for EUV (MORE) / J. Passarelli, M. Murphy, R.D. Re et al. // Adwances in Patterning Materials and Processes XXXII. – 2015. – V. 9425, № 94250T. DOI: 10.1117/12.2086599.

Cardenas-Trivino, G. Synthesis and Molecular Weights of Metal Poly(methyl methacrylates) / G. Cardenas-Trivino, C. Retamal, K.J. Klabunde // Polym. Bull. – 1991. – V. 25, № 3. – P. 315–318. DOI: 10.1007/BF00316900.

Cardenas-Trivino, G. Thermogravimetric Studies of Metal Poly(Methylmethacrylates) / G. Cardenas-Trivino, C. Retamal, L.H. Tagle // Thermochim. Acta. – 1991. – V. 176. – P. 233–240. DOI: 10.1016/0040-6031(91)80278-Q.

Naka, K. Ring-Collapsed Radical Alternating Copolymerization of Phenyl-Substituted Cyclooligostibine and Acetylenic Compounds / K. Naka, A. Nakahashi, Y. Chujo // Macromolecules. – 2006. – V. 39. № 24. – P. 8257–8262. DOI: 10.1021/ma061220l.

Naka, K. Periodic Terpolymerization of Cyclooligoarsine, Cyclooligostibine, and Acetylenic Compound / K. Naka, A. Nakahashi, Y. Chujo // Macromolecules. – 2007. – V. 40, № 5. – P. 1372–1376. DOI: 10.1021/ma0622332.

Котон, М.М. Металлоорганические соединения и радикалы / М.М. Котон. – М.: Наука, 1985. – С. 13.

Карраер, Ч. Металлоорганические полимеры / Ч. Карраер, Дж. Шитс, Ч. Питтмен. – М.: Мир, 1981. – 352 с.

Диакрилаты трифенилвисмута и трифенилсурьмы в синтезе металлосодержащего полиметилметакрилата / В.А. Додонов, А.В. Гущин, Ю.Л. Кузнецова, В.А Моругова // Вестник ННГУ. Серия химия. – 2004. – Вып. 1(4). – С. 86–94.

Kensuke, N. Ring-Collapsed Radical Alternating Copolymerization of Phenyl-Substituted Cyclooligostibine and Acetylenic Compounds / N. Kensuke, N. Akiko, C. Yoshiki // Macromolecules. – 2006. – V. 39(24). – P. 8257–8262. DOI: 10.1021/ma061220l.

Brief Note Improved Methods for the Synthesis of Antimony Triacetate, Triphenylantimony Diacetate, and Pentaphenylantimony / T.C. Thepe, R.I. Garascia, M.A. Selvoski, A.N. Pattel // Ohio S. Sci. – 1977. – V. 77, № 3. – P. 134–135.

Synthesis, Structure, and Spectroscopic Properties of Copper(II) Compounds Containing Nitrogen-Sulphur Donor Ligands; the Crystal and Molecular Structure of Aqua[l,7-bis(N-methylbenzimidazol-2'-yl)- 2,6-dithiaheptane]copper(II) Perchlorate / A.W. Addison, T.N. Rao, J. Reedijk et al. // J. Chem. Soc., Dalton Trans. – 1984. – № 7. – P. 1349–1356. DOI: 10.1039/DT9840001349.

Adams, E.A. Structure of Triphenylstibine / E.A. Adams, J.W. Kolis, W.T. Pennington // Acta Crystallogr., Sect. C: Struct. Chem. – 1990. – C46(5). P. 917–919. DOI: 10.1107/S0108270189012862.

Batsanov, S.S. Van der Waals Radii of Elements / S.S. Batsanov // Inorg. Mater. – 2001. – V. 37, № 9. – P. 871–885.

Синтез и строение диакрилата трифенилсурьмы / А.В. Гущин, Л.К. Прыткова, Д.В. Шашкин и др. // Вестник ННГУ. – 2010. – Т. 3, Вып. 1. – С. 95–99.

Oswald, I.D.H. Polymorphism and Polymerisation of Acrylic and Methacrylic Acid at High Pressure / I.D.H. Oswald, A.J. Urquhart // CrystEngComm. – 2011. – V. 13. – P. 4503–4507. DOI: 10.1039/c1ce05295k.

Synthesis and Structure of Triphenylantinony Dimethacrylate / A.V. Gushchin, D.V. Shashkin, L.K. Prytkova et al. // Russ. J. Gen. Chem. – 2011. – V. 81, № 3. – P. 493–396. DOI: 10.1134/S107036321103008X.

Синтез и строение дикротоната трифенилсурьмы / А.В. Гущин, О.С. Калистратова, Р.А. Верховых и др. // Вестник ННГУ. – 2013. – № 1(1). – С. 86–90.

Topochemical Studies. III. The Crystal and Molecular Structures of Crotonic Acid, CH3CH= CHCOOH, and Crotonamide, CH3CH=CHCONH2 / S. Shimizu, S. Kekka, S. Kashino, M. Haisa // Bull. Chem. Soc. Jpn. – 1974. – V. 47, iss. 7. – P. 1627–1631. DOI: 10.1246/bcsj.47.1627.

Synthesis and Structure of Bis[(2E)-3-(2-furyl)prop-2-enoato]triphenylantimony Ph3Sb[O2CCH=CH(C4H3O)]2 / O.S. Kalistratova, P.V. Andreev, A.V. Gushchin et al. // Crystallogr. Rep. – 2016. – V. 61, № 3. – P. 391–394. DOI: 10.1134/S1063774516030135.

Filippakis, S.E. Topochemistry. Part XVI. The Crystal Structure of trans-β-2-Furylacrylic Acid / S.E. Filippakis, G.M.J. Schmidt // J. Chem. Soc. (B). – 1967. – P. 229–232. DOI:10.1039/J29670000229.

Experimental Study of Electron Density Distribution in Crystals of Antimony(V) Dicarboxylate Complexes / G.K. Fukin, M.A. Samsonov, O.S. Kalistratova, A.V. Gushchin // Struct. Chem. – 2016. – V. 27, № 1. – P. 357–365.

Bryan, R.F. Crystal Structures of α-Trans- and p-Methoxy-cinnamic Acids and Their Relation to Thermal Mesomorphism / R.F. Bryan, D.P. Freyberg // J. Chem. Soc., Perkin Trans. 2 – 1975. – P. 1835–1840. DOI: 10.1039/P29750001835.

Cинтез нового производного трифенилсурьмы с мета-нитрокоричной кислотой и исследование его строения методами ИК-, ЯМР-спектроскопии / А.В. Гущин, О.С. Калистратова, Р.А. Верховых и др. // Вестник ННГУ. – 2013. – № 2(1). – С. 69–70.

3-Nitrocinnamic Acid / K.U. Lakshmi, S. Thamotharan, M. Srinivasan et al. // Acta Crystallographica. Section E. – 2005. – E. 61. – P. 3636–3638. DOI: 10.1107/S1600536805031879.

Bis[(E)-3-(4-methoxyphenyl)prop-2-enoato]triphenylantimony(V) Benzene Monosolvate / P.V. Andreev, N.V. Somov, O.S. Kalistratova et al. // Acta Crystallogr., Sect. E: Crystallogr. Commun. – 2013. – V. 69, № 3. – m167. DOI: 10.1107/S1600536813004674.

Cox, P.J. Sorbic Acid / P.J. Cox // Acta Crystallogr., Sect. C: Struct. Chem. – 1994. – C50. – P. 1620–1622. DOI: 10.1107/S0108270194002891.

Suzuki, H. Organobismuth Chemistry / H. Suzuki, Y. Matano // Amsterdam, Elsever, 2001. – 619 p.

Розенберг, А.С. Формирование наноразмерных частиц при твердофазных термических превращениях карбоксилатов металлов / А.С. Розенберг, Г.И. Джардималиева, А.Д. Помогайло // Докл. Акад. наук. – 1997. – Т. 356, № 1. – С. 66–69.

Preparation and Reactivity of Metal-Containing Monomers. 21. Spontaneous Polymerization of Acrylamide Coordinated to Metal Nitrates / V.S. Savost'yanov, V.N. Vasilets, O.V. Ermakov et al. // Russ. Chem. Bull. – 1992. – V. 41, iss. 9. – P. 1615–1620.

Исследование термической полимеризации акрилатов кобальта (II) и никеля (II) методом диэлектрической спектроскопии / Г.Ф. Новиков, И.А. Чернов, Г.И. Джардималиева, А.Д. Помогайло // Конденсированные среды и межфазные границы. – 2005. – Т. 7, № 3. – С. 239–248.

Hirschfeld, F.L. Topochemical Control of Solid-State Polymerization / F.L. Hirschfeld, G.M.J. Schmidt // J. Polymer Sci. – 1964. – V. 2, Iss. 5. – P. 2181–2190. DOI: 10.1002/pol.1964.100020513.

Shklover, V.E. Structural Aspects of Solid-phase Polymerisation / V.E. Shklover, N.G. Bokii, Y.T. Struchkov // Russ. Chem. Rev. – 1977. – V. 46, Iss. 8. – P. 706–721. DOI: 10.1070/RC1977v046n08ABEH002167.

Janiak, C. A Critical Account on π–π Stacking in Metal Complexes with Aromatic Nitrogen-Containing Ligands / C. Janiak // J. Chem. Soc., Dalton Trans. – 2000. – № 21. – P. 3885–3896. DOI: 10.1039/b003010o.

Experimental and Theoretical Distribution of Electron Density and Thermopolimerization in Crystals of Ph3Sb(O2CCH=CH2)2 Complex / G.K. Fukin, M.A. Samsonov, A.V. Arapova et al. // J. Solid State Chem. – 2017. – V. 254. – P. 32–39. DOI: 10.1016/j.jssc.2017.06.030.

Калориметрическое изучение диакрилата и диметакрилата трифенилсурьмы / И.А. Летянина, А.В. Маркин, Н.Н. Смирнова, А.В. Гущин // Вестник ННГУ. Серия химия. – 2012. – № 3(1). – С. 105–110.

Calorimetric Study of Organic Compounds of Antimony and Bismuth Ph3Sb(O2CCH=CHCH3)2 and Ph3Bi(O2CCH=CHCH3)2 / I.A. Letyanina, A.V. Markin, N.N. Smirnova et al. // J. Therm. Anal. Calorim. – 2016. – V. 125, iss. 1. – P. 339–349. DOI: 10.1007/s10973-016-5401-2.

Molecular and Crystalline Structure of Pyrocatechol and Hydroquinone Dimethacrylates and Their Reactivity in Melts / S.A. Chesnokov, G.K. Fukin, Yu.V. Chechet et al. // Polym. Sci., Part A. – 2006. – V. 48, № 6. – P. 606–611. DOI: 10.1134/S0965545X06060083.

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Published

2019-08-19

Issue

Vol. 11 No. 3 (2019): Вестник Южно-Уральского государственного университета. Серия: Химия

Section

Химия элементоорганических соединений