Studies on the Halogen Substituted β-Amino Acids and Their Cu(Ⅱ) Coordination Complexes in Crystallography

doi:10.1007/s40242-016-5333-1

Abstract

Abstract:

Halogen substituted β-amino acids, D,L-3-amino-3-(4-fluoro)phenylpropionic acid(D,L-HL1, 1) and D,L-3-amino-3-(4-bromo)phenylpropionic acid(D,L-HL2, 2), as well as their Cu(Ⅱ) coordination complexes[Cu(L1)₂(CH₃OH)₂]·2CH₃OH(3) and[Cu(L2)₂(CH₃OH)₂]·2CH₃OH(4) were investigated and their single crystal structures were discussed in details. Supramolecular helical chains were found in β-amino acids 1 and 2 while there was no helix in their coordination complexes 3 and 4. The formation of supramolecular helixes could be due to the hydrogen bonds between terminal-NH³⁺ and adjacent-COO^- in β-amino acids 1 and 2. While, this kind of hydrogen bonds could not be observed in their Cu(Ⅱ) coordination complexes 3 and 4, in which central-symmetrical dimers could be formed via coplanar coordinated bonds(N-Cu-O) between-NH₂ and-COO^-.

Key words: β-Amino acid, Copper, H-Bonding, Halogen, Crystal structure

ZHENG Chunying, QIU Qiming, HAO Liang, LI Hui. Studies on the Halogen Substituted β-Amino Acids and Their Cu(Ⅱ) Coordination Complexes in Crystallography[J]. Chemical Research in Chinese Universities, 2016, 32(1): 1-7.

References

[1] Zhang Y., Li L., Yuan W., Zhang X., Chem. Res. Chinese Universities, 2015, 31(3), 381
[2] Wang J., Luo X., Yuan Y., Zhang L., Chem. Res. Chinese Universities, 2015, 31(4), 503
[3] van Hecke K., Cardinaels T., Nockemann P., Jacobs J., Vanpraet L., Parac-Vogt T. N., Binnemans K., van Meervelt L., Angew. Chem. Int. Ed., 2014, 53(34), 8959
[4] Li S., Sun W., Wang K., Ma H., Pang H., Liu H., Zhang J., Inorg. Chem., 2014, 53(9), 4541
[5] Huang Z. G., Kang S. K., Banno M., Yamaguchi T., Lee D., Seok C., Yashima E., Lee M., Science, 2012, 337(6101), 1521
[6] Falkowski J. M., Liu S., Wang C., Lin W. B., Chem. Commun., 2012, 48(52), 6508
[7] Hu B., Tao T., Bin Z. Y., Peng Y. X., Ma B. B., Huang W., Cryst. Growth Des., 2014, 14(1), 300
[8] Kurahashi T., Hada M., Fujii H., Inorg. Chem., 2014, 53(2), 1070
[9] Zhou P., Yao J. F., Sheng C. F., Li H., Cryst. Eng. Comm., 2013, 15(42), 8430
[10] Sanz M. E., Lesarri A., Peña M. I., Vaquero V., Cortijo V., López J. C., Alonso J. L., J. Am. Chem. Soc., 2006, 128(11), 3812
[11] Prikhodchenko P. V., Medvedev A. G., Tripol'skaya T. A., Churakov A. V., Wolanov Y., Howardc J. A. K., Lev O., Cryst. Eng. Comm., 2011, 13(7), 2399
[12] Dong L., Zheng C., Zhou P., Shi R., Li H., Acta Chim. Sinica, 2014, 72(9), 981
[13] Baran J., Drozd M., Ratajczak H., Pietraszko A., J. Mol. Struct., 2009, 927(1), 43
[14] Kandasamy A., Siddeswaran R., Murugakoothan P., Suresh Kumar P., Mohan R., Cryst. Growth. Des., 2007, 7(2), 183
[15] Jarmelo S., Reva I., Rozenberg M., Silva M. R., Beja A. M. M., Fausto R., J. Phys. Chem. B, 2008, 112(27), 8032
[16] Wilkinson H. S., Harrison W. T. A., Acta Cryst. C, 2005, 61(6), m²53
[17] Donohue J., J. Am. Chem. Soc., 1950, 72(2), 949
[18] Kolesov B. K., Minko V. S., Boldyreva E. V., Drebushchak T. N., J. Phys. Chem. B, 2008, 112(40), 12827
[19] Vasily S., Minkov V. S., Tumanov N. A., Cryst. Eng. Comm., 2010, 12(9), 2551
[20] Hübschle C. H., Messerschmidt M., Luger M., Cryst. Res. Technol., 2004, 39(3), 274
[21] Iwama S., Horiguchi M., Sato H., Uchida Y., Takahashi H., Tsue H., Tamura R., Cryst. Growth Des., 2010, 10(6), 2668
[22] Konno T., Yoshimura T., Aoki K., Okamoto K., Hirotsu M., Angew. Chem. Int. Ed., 2001, 40(9), 1765
[23] Leung B. O., Jalilehvand F., Mah V., Parvez M., Wu Q., Inorg. Chem., 2013, 52(8), 4593
[24] Wojciechowska A., Daszkiewicz M., Staszak Z., Trusz-Zdybek A., Bienko A., Ozarowskiz A., Inorg. Chem., 2011, 50(22), 11532
[25] Lou B. Y., Jiang F. L., Wu B. L., Yuan D. Q., Hong M. C., Cryst. Growth Des., 2006, 6(4), 989
[26] Konar A. D., Cryst. Eng. Comm., 2013, 15(13), 2466
[27] Abirami S., Xing Y. M., Tsang C. W., Ma N. L., J. Phys. Chem. A, 2005, 109(3), 500
[28] Sewald N., Angew. Chem. Int. Ed., 2003, 42(47), 5794
[29] Frackenpohl J., Arvidsson P. I., Schreiber J. V., Seebach D., Chem. Bio. Chem., 2001, 2(6), 445
[30] Jin L. L., Lei Y. T., Chem. Res. Chinese Universities, 2013, 29(4), 710
[31] Seebach D., Gardiner J., Acc. Chem. Res., 2008, 41(10), 1366
[32] Fülöp F., Martikek T. A., Tóth G. K., Chem. Soc. Rev., 2006, 35(4), 323
[33] Porter E. A., Wang X., Lee H., Weisblum B., Gellman S. H., Nature, 2000, 404(6778), 565
[34] Specker E., Bottcher J., Lilie H., Heine A., Schoop A., Muller G., Griebenow N., Klebe G., Angew. Chem. Int. Ed., 2005, 44(20), 3140
[35] Myers A. G., Barbay J. K., Zhong B., J. Am. Chem. Soc., 2001, 123(30), 7207
[36] Drouet F., Noisier A. F. M., Harris C. S., Furkert D. P., Brimble M. A., Eur. J. Org. Chem., 2014, 2014(6), 1195
[37] Salwiczek M., Nyakatura E. K., Gerling U. I. M., Ye S., Koksch B., Chem. Soc. Rev., 2012, 41(6), 2135
[38] Buer B. C., Marsh E. N. G., Protein Sci., 2012, 21(4), 453
[39] Yuvienco C., More H. T., Haghpanah J. S., Tu R. S., Montclare J. K., Biomacromolecules, 2012, 13(8), 2273
[40] Kim W., Hardcastle K. I., Conticello V. P., Angew. Chem. Int. Ed., 2006, 45(48), 8141
[41] Puga A. V., Teixidor F., Sillanp R., Chem. Eur. J., 2009, 15(38), 9764
[42] Guillermo M. E., Lee B., David R. A., J. Am. Chem. Soc., 2008, 130, 9058
[43] Metrangelo P., Meyer F., Pilati T., Resnati G., Terraneo G., Angew. Chem. Int. Ed., 2008, 47(33), 6114
[44] Desiraju G. R., Nature, 2001, 412(6845), 397
[45] Aakeröy C. B., Chopade P. D., Desper J., Cryst. Growth Des., 2011, 11(12), 5333
[46] Tero T. R., Salorinne K., Nissinen M., Cryst. Eng. Comm., 2012, 14(21), 7360
[47] Cariati E., Forni A., Biella S., Metrangolo P., Meyer F., Resnati G., Righetto S., Tordin E., Ugo R., Chem. Commun., 2007, (25), 2590
[48] Kudo F., Miyanagaa A., Eguchi T., Nat. Prod. Rep., 2014, 31(8), 1056
[49] Weiner B., Szymanski W., Janssen D. B., Minnaarda A. J., Feringa B. L., Chem. Soc. Rev., 2010, 39(5), 1656
[50] Saha M. K., Bernal I., Chem. Commun., 2003, (5), 612
[51] Gasque L., Verhoeven M. A., Bernès S., Barrios F., Haasnoot J. G., Reedijk J., Eur. J. Inorg. Chem., 2008, (28), 4395
[52] Gerasimenko A. V., Davidovich R. L., Logvinova V. B., J. Mol. Struct., 2011, 52(3), 524
[53] Beaumont S., Pons V., Retailleau P., Dodd R. H., Dauban P., Angew. Chem. Int. Ed., 2010, 49(9), 1634
[54] Tana C. Y. K., Weaver D. F., Tetrahedron, 2002, 58(37), 7449
[55] Bruker, SMART and SAINT, Bruker AXS Inc., Madison, 2002
[56] Sheldrick G. M., Acta Crystallogr. Sect. A, 2008, 64, 112
[57] Chopra D., Nagarajan K., Guru R. T. N., Cryst. Growth Des., 2005, 5(3), 1035
[58] Minkov V. S., Chesalov Y. A., Boldyreva E. V., J. Struct. Chem., 2010, 51(6), 1052
[59] Ramachandran E., Natarajan S., Cryst. Res. Technol., 2006, 41(4), 411
[60] Gao E. Q., Yue Y. F., Bai S. Q., He Z., Yan C. H., J. Am. Chem. Soc., 2004, 126(5), 1419
[61] Rao A. S., Pal A., Ghosh R., Das S. K., Inorg. Chem., 2009, 48(5), 1802
[62] Tian G., Zhu G. S., Yang X.Y., Fang Q. R., Xue M., Sun J. Y., Wei Y., Qiu S. L., Chem. Commun., 2005, (11), 1396
[63] Christenholz C. L., Obenchain D. A., Peebles R. A., Peebles S. A., J. Phys. Chem. A, 2014, 118(9), 1610
[64] Alonso J. L., Antolínez S., Blanco S., Lesarri A., Lopez J. C., Caminati W., J. Am. Chem. Soc., 2004, 126(10), 3244
[65] Asensio G., Medio-Simon M., Alemán P., Ramírez de Arellano C., Cryst. Growth Des., 2006, 6(12), 2769
[66] Murray-Rust P., Stallings W. C., Monti C. T., Preston R. K., Glusker J. P., J. Am. Chem. Soc., 1983, 105(10), 3206
[67] Schwarzer A., Seichter W., Weber E., Stoeckli-Evans H., Losadac M., Hulliger J., Cryst. Eng. Comm., 2004, 6, 567
[68] Pavan M. S., Pal R., Nagarajan K., Guru R. T. N., Cryst. Growth Des., 2014, 14(11), 5477
[69] Berger R., Resnati G., Metrangolo P., Weber E., Hulliger J., Chem. Soc. Rev., 2011, 40(7), 3496
[70] Metrangolo P., Murray J. S., Pilati T., Politzer P., Resnati G., Terraneo G., Cryst. Eng. Comm., 2011, 13(22), 6593
[71] Desiraju G. R., Parthasarathy R., J. Am. Chem. Soc., 1989, 111(23), 8725
[72] Bailey A. J., Lee C., Feller R. K., Orton J. B., Mellot-Draznieks C., Slater B., Harrison W. T. A., Simoncic P., Navrotsky A., Grossel M. C., Cheetham A. K., Angew. Chem. Int. Ed., 2008, 47(120), 8634
[73] Chen S., Zhang J., Bu X., Inorg. Chem., 2009, 48(14), 6356