ESTERS OF DIPHENYLPHOSPHINOSELENOTHIOIC AND DIPHENYLPHOSPHINODISELENOIC ACIDS WITH POTENTIAL FOR RAFT POLYMERIZATION

Authors

  • Nora CHIOREAN Department of Chemistry, Supramolecular Organic and Organometallic Chemistry Centre (SOOMCC), Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, Cluj-Napoca, Romania. Corresponding author: ancas@chem.ubbcluj.ro.
  • Alexandra POP Department of Chemistry, Supramolecular Organic and Organometallic Chemistry Centre (SOOMCC), Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, Cluj-Napoca, Romania. Email: alexandra.m.pop@ubbcluj.ro. https://orcid.org/0000-0002-2355-3682
  • Cristian SILVESTRU Department of Chemistry, Supramolecular Organic and Organometallic Chemistry Centre (SOOMCC), Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, Cluj-Napoca, Romania. Email: cristian.silvestru@ubbcluj.ro. https://orcid.org/0000-0001-5124-9525
  • Anca SILVESTRU Department of Chemistry, Supramolecular Organic and Organometallic Chemistry Centre (SOOMCC), Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, Cluj-Napoca, Romania. Email: ancas@chem.ubbcluj.ro. https://orcid.org/0000-0002-0942-581X

DOI:

https://doi.org/10.24193/subbchem.2019.2.16

Keywords:

organophosphorus(V) compounds, organoselenium compounds; intramolecular coordination; solution behavior, solid state structure

Abstract

Compounds of type Ph2P(E)SeR [E = S, R = 2-MeC6H4 (1), 2-(Me2NCH2)C6H4 (2); E = Se, R = 2-(Me2NCH2)C6H4 (3)], were prepared and structurally characterized in solution by multinuclear NMR (1H, 31P, 77Se). The attempts to obtain the derivative Ph2P(S)SeC6H4(CH2NMePri)-2 (4) resulted in a complex mixture. The attempts to separate the components resulted in further decomposition and hydrolysis and the isolated crystals were investigated by single-crystal X-ray diffraction when proved to be the ammonium salt [MePriBnNH]+[Ph2P(S)O]ˉ (Bn = benzyl) (4a).

References

X. Tian, J. Ding, B. Zhang, F. Qiu, X. Zhuang, Y. Chen, Polymers, 2018, 10, 318.

C. Barner-Kowollik, T.P. Davis, J.P. A. Heuts, M.H. Stenzel, P. Vana, M. Whittaker, J. Polym. Sci., Part A: Polym. Chem., 2003, 41, 365.

D.J. Keddie, G. Moad, E. Rizzardo, S.H. Thang, Macromolecules, 2012, 45, 5321.

C. Konn, F. Morel, D.L. Beyou, P. Chaumont, E. Bourgeat-Lami, Macromolecules, 2007, 40, 7464.

J. Nicolas, Y. Guillaneuf, C. Lefay, D. Bertin, D. Gigmes, B. Charleux, Prog. Polym. Sci., 2013, 38, 63.

N.V. Tsarevsky, K. Matyjaszewski, Chem. Rev., 2007, 107, 2270.

J. Ran, L. Wu, Z. Zhang, T. Xu, Prog. Polym. Sci., 2014, 39, 124.

A. Alberti, M. Benaglia, M. Laus, K. Sparnacci, J. Org. Chem., 2002, 67, 7911.

D. Gigmes, D. Bertin, S. Marque, O. Guerret, P. Tordo, Tetrahedron Lett., 2003, 44, 1227.

J.L. Hodgson, K.A. Green, M.L Coote, Org. Lett., 2005, 7, 4581.

J. Moon, H. Nam, S. Kim, J. Ryu, C. Han, C. Lee, S. Lee, Tetrahedron Lett., 2008, 49, 5137.

T. Kimura, T. Murai, J. Org. Chem., 2005, 70, 952.

R. Şuteu, S. Shova, A. Silvestru, Inorg. Chim. Acta, 2018, 475, 105.

A. Covaci, R. Mitea, I. Hosu, A. Silvestru, Polyhedron, 2014, 72, 157.

A. Pop, A. Silvestru, E.J. Juárez-Pérez, M. Arca, V. Lippolis, C. Silvestru, Dalton Trans., 2014, 43, 2221.

R.A. Popa, E. Licarete, M. Banciu, A. Silvestru, Appl. Organomet. Chem., 2018, 32, e4252.

R. Mattes, D. Rühl, Acta Crystallogr., Sect. C: Struct. Chem., 1984, C40, 106.

J. Emsley, “Die Elemente“, Walter de Gruyter, Berlin, 1994.

M.W. Schmidt, P.H. Truong, M.S. Gordon, J. Am. Chem. Soc., 1987, 109, 5217.

H. Ahlbrecht, J. Harbach, R.W. Hoffmann, T. Ruhland, Liebigs Ann., 1995, 211.

MestReC and MestReNova, Mestrelab Research S.L., Feliciano Barrera 9B, Bajo, 15706 Santiago de Compostela, Spain, 2015.

G.M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 2008, A64, 112.

DIAMOND, Visual Crystal Structure Information System, Crystal Impact, Postfach 1251, 53002 Bonn, Germany, 2015.

STUDIA UBB CHEMIA, Volume 64 (LXIV), No.2, Tome I, June 2019

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Published

2019-06-03

How to Cite

CHIOREAN, N. ., POP, A. ., SILVESTRU, C. ., & SILVESTRU, A. . (2019). ESTERS OF DIPHENYLPHOSPHINOSELENOTHIOIC AND DIPHENYLPHOSPHINODISELENOIC ACIDS WITH POTENTIAL FOR RAFT POLYMERIZATION. Studia Universitatis Babeș-Bolyai Chemia, 64(2), 197–206. https://doi.org/10.24193/subbchem.2019.2.16

Issue

Volume 64, No. 2, Tome I, 2019

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