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Linking Nitrate and Dihydrogenphosphate Motifs with N,N',N"-Triisopropylguanidinium Cation: Syntheses and Structures of NO3– and H2PO4– Salts
Corresponding Author(s) : Farouq F. Said
Asian Journal of Chemistry,
Vol. 25 No. 15 (2013): Vol 25 Issue 15
Abstract
The trisubstituted guanidine N,N',N"-triisopropylguanidine (TPG) reacts with ammonium nitrate in water and with phosphoric acid in THF to produce (TPGH)2(NO3)2(H2O) (1) and (TPGH)2(H2PO4)2(H3PO4) (2) salts. Compounds 1 and 2 were characterized by X-ray diffraction analysis and the two structures displayed two crystallographically unique cations. A complex hydrogen-bonding scheme operates in 1 between the guanidinium cation and nitrate anion via N–H···O and O–H···O synthons. The primary structure of 2 is the formation of dihydrogenphosphate anion chains along the c-axis direction through O–H···O synthon, which are triply-crossed by the 3-fold cations consolidating a 3-D structure. Compound 1 crystallized in the monoclinic space group P2(1)/n, where a = 16.841(5) Å, b = 9.122(3) Å, c = 19.926(6) Å, b = 95.041(6)º and compound 2 crystallized in the monoclinic system space group P2(1)/c with a = 16.542(2) Å, b = 10.8515(16) Å, c = 18.702(3) Å, b = 91.888º(3).
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- M.D. Best, S.L. Tobey and E.V. Anslyn, Coord. Chem. Rev., 240, 3 (2003).
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References
M.D. Best, S.L. Tobey and E.V. Anslyn, Coord. Chem. Rev., 240, 3 (2003).
C.L. Hanon and E.V. Anslyn, Bioorg. Chem. Frontiers, 3, 193 (1993).
D.M. Perrault, L.A. Cabell and E.V. Anslyn, Bioorg. Med. Chem., 5, 1209 (1997).
A. Metzger, V.M. Lynch and E.V. Anslyn, Angew. Chem. Int. Ed. Engl., 36, 862 (1997).
K.A. Schung and W. Lindner, Chem. Rev., 105, 67 (2005).
M. Dincer, N. Ozdemir, E. Saripinar, L. Kulak and O. Buyukgungor, Acta Cryst. C, C61, o722 (2005).
F.A. Cotton, V.W. Day, E.E. Hazen and S. Larsen, J. Am. Chem. Soc., 95, 4834 (1973).
F.F. Said, P. Bazinet, T.-G. Ong, G.P.A. Yap and D. Richeson, Cryst. Growth Des., 5, 1881 (2005).
F.F. Said, P. Bazinet, T.-G. Ong, G.P.A. Yap and D. Richeson, Cryst. Growth Des., 6, 258 (2006).
F.F. Said, P. Bazinet, G.P.A. Yap and D. Richeson, Cryst. Growth Des., 6, 1848 (2006).
F.F. Said, B.F. Ali and D. Richeson, Acta Cryst., E67, O3467 (2011).
F.F. Said, B.F. Ali, D. Richeson and I. Korobkov, Acta Cryst., E68, o1906 (2012).
T.G. Ong, G.P.A. Yap and D.S. Richeson, J. Am. Chem. Soc., 125, 8100 (2003); T.G. Ong, G.P.A. Yap and D.S. Richeson, Organometallics, 22, 387 (2003); N. Thirupathi, G.P.A. Yap and D.S. Richeson, Chem. Commun., 2483 (1999); M.K.T. Tin, N. Thirupathi, G.P.A. Yap and D.S. Richeson, J. Chem. Soc., Dalton Trans., 2947 (1999); M.K.T. Tin, G.P.A. Yap and D.S. Richeson, Inorg. Chem., 37, 6728 (1998).
B.F. Abrahams, M.G. Haywood, T.A. Hudson and R. Robson, Angew. Chem. Int. Ed., 43, 6157 (2004).
B.F. Abrahams, M.G. Haywood, T. A. Hudson and R. Robson, J. Am. Chem. Soc., 127, 816 (2005).
K.T. Holman,A.M. Pivovar and M.D. Ward, Science, 294, 1907 (2001).
K.T. Holman,A.M. Pivovar, A.M. Swift, J.A. and M.D. Ward, Acc. Chem. Res., 34, 107 (2001).
W.T.A. Harrison, M.L.F. Phillips, W. Clegg and S.J Teat, J. Solid State Chem., 148, 433 (1999).
T. Steiner, Angew. Chem. Int. Ed., 41, 48 (2002).
D.R. Trivedi,A. Ballabh and P. Dastidar, CrystEngComm., 5, 358 (2003).
A. Ballabh, D.R. Trivedi, P. Dastidar and E. Suresh, CrystEngComm., 4, 135 (2002).
J.C. MacDonald, P.C. Dorrestein and M.M. Pilley, Cryst. Growth Des., 1, 29 (2001).
C.B. Aakeroy and M. Nieuwenhuyzen, J. Am. Chem. Soc., 116, 10983 (1994).
C.B. Aakeroy, P.B. Hitchcock and K.R. Seddon, Chem. Commun., 553 (1992).
J. Emsley, Chem. Soc. Rev., 9, 91 (1980).
J.C. Speakman, Struct. Bond., 12, 141 (1972).
T. Steiner, Acta Crystallogr., B57, 103 (2001).
A. Gobbi and G. Frenking, J. Am. Chem. Soc., 115, 2362 (1993)