2
46
N. Chakrabarti et al. / Polyhedron 58 (2013) 235–246
(
i) H.K. Joshi, M.E. Arvin, J.C. Durivage, N.E. Gruhn, M.D. Carducci, B.L.
[23] For other examples of lithium aqua compounds that do not feature hydrogen
bonding interactions, see:
Westcott, D.L. Lichtenberger, J.H. Enemark, Polyhedron 23 (2004) 429;
(
(
(
(
(
(
(
j) H.V.R. Dias, T. Goh, Polyhedron 23 (2004) 273;
k) C.P. Olmo, K. Bohmerle, G. Steinfeld, H. Vahrenkamp, Eur. J. Inorg. Chem.
2006) 3869;
l) M.H. Chisholm, J.C. Gallucci, G. Yaman, Inorg. Chem. 46 (2007) 8676;
m) S.R. Batten, M.B. Duriska, P. Jensen, J.Z. Lu, Aust. J. Chem. 60 (2007) 72;
n) M.H. Chisholm, J.C. Gallucci, G. Yaman, Chem. Commun. (2006) 1872;
o) Z.B. Hu, S.M. Gorun, Inorg. Chem. 40 (2001) 667.
(a) J.M. Butler, G.M. Gray, J. Chem. Crystallogr. 33 (2003) 557;
(b) Y. Yokota, R.A. Jacobson, B.C. Logsdon, S. Ringrose, A.T. Setterdahl, J.G.
Verkade, Polyhedron 18 (1999) 2519;
(c) J.M. Butler, G.M. Gray, J. Chem. Crystallogr. 32 (2002) 171;
(d) H.-J. Haupt, M. Schwefer, H. Egold, U. Flörke, Inorg. Chem. 36 (1997) 184;
(e) S. Schütte, U. Pieper, U. Klingebiel, D. Stalke, J. Organomet. Chem. 446
(1993) 45;
[
[
8] W. Sattler, G. Parkin, J. Am. Chem. Soc. 133 (2011) 9708.
9] (a) S. Trofimenko, J.C. Calabrese, J.S. Thompson, Inorg. Chem. 26 (1987) 1507;
(f) P.K. Bakshi, S.V. Sereda, O. Knop, M. Falk, Can. J. Chem. 72 (1994) 2144;
(g) H. Schödel, T. Vaupel, H. Bock, Acta Crystallogr., Sect. C Cryst. Struct.
Commun. 52 (1996) 637.
(
b) S. Trofimenko, J.C. Calabrese, J.K. Kochi, S. Wolowiec, F.B. Hulsbergen, J.
Reedijk, Inorg. Chem. 31 (1992) 3943.
10] (a) See, for example: J.L. Kisko, T. Hascall, C. Kimblin, G. Parkin, J. Chem. Soc.,
Dalton Trans. (1999) 1929;
[24] For other examples of lithium aqua compounds that exhibit hydrogen bonding
to pyrazoles, see:
(a) O. Moers, A. Blaschette, P.G. Jones, Z. Anorg. Allg. Chem. 628 (2002) 377;
(b) T.M. Klapotke, C.M. Sabate, J.M. Welch, Dalton Trans. (2008) 6372.
[25] For other examples of lithium aqua compounds that exhibit hydrogen bonding
to THF, see:
[
[
[
[
(
(
(
(
b) D.J. Brauer, H. Burger, G.R. Liewald, J. Wilke, J. Organomet. Chem. 287
1985) 305;
c) R. Campbell, P. Garcia-Alvarez, A.R. Kennedy, R.E. Mulvey, Chem. Eur. J. 16
2010) 9964.
(a) E.D. Gueneau, K.M. Fromm, H. Goesmann, Chem. Eur. J. 9 (2003) 509;
(b) R.D. Bergougnant, A.Y. Robin, K.M. Fromm, Tetrahedron 63 (2007) 10751;
(c) A. Bilyk, A.K. Hall, J.M. Harrowfield, M.W. Hosseini, B.W. Skelton, A.H.
White, Inorg. Chem. 40 (2001) 672.
11] See, for example:
(
(
(
a) K.W. Henderson, A.E. Dorigo, Q.Y. Liu, P.G. Williard, J. Am. Chem. Soc. 119
1997) 11855;
b) D.M. Cousins, M.G. Davidson, C.J. Frankis, D. Garcia-Vivo, M.F. Mahon,
[26] (a) L. Fielding, Tetrahedron 56 (2000) 6151;
Dalton Trans. 39 (2010) 8278;
c) J.K. Brask, T. Chivers, G.P.A. Yap, Chem. Commun. (1998) 2543.
12] (a) K. Pang, Y. Rong, G. Parkin, Polyhedron 29 (2010) 1881;
b) L.M. Engelhardt, J.M. Harrowfield, M.F. Lappert, I.A. Mackinnon, B.H.
Newton, C.L. Raston, B.W. Skelton, A.H. White, Chem. Commun. (1986) 846;
(b) L. Fielding, Prog. Nucl. Magn. Reson. Spectrosc. 51 (2007) 219;
(c) R. Mathur, N.C. Li, E.D. Becker, R.B. Bradley, J. Phys. Chem. 67 (1963) 2190;
(d) M.W. Hanna, A.L. Ashbaugh, J. Phys. Chem. 68 (1964) 811.
[27] (a) M.G. Voronkov, Pure Appl. Chem. 13 (1966) 35;
(b) M.G. Voronkov, V.P. Baryshok, J. Organomet. Chem. 239 (1982) 199;
(c) M.G. Woronkow, G.I. Seltschan, A. Lapsina, W.A. Pestunowitschich, Z.
Chem. 8 (1968) 214.
[28] (a) J.G. Verkade, Coord. Chem. Rev. 137 (1994) 233;
(b) J.G. Verkade, Acc. Chem. Res. 26 (1993) 483.
[29] (a) A.F. Hill, G.R. Owen, A.J.P. White, D.J. Williams, Angew. Chem., Int. Ed. 38
(1999) 2759;
(
(
(
(
(
c) Z.X. Wang, Z.Y. Chai, Y. Li, J. Organomet. Chem. 690 (2005) 4252;
d) A.R. Kennedy, J. Klett, R.E. Mulvey, S. Newton, D.S. Wright, Chem. Commun.
2008) 308.
13] S.L. Guo, F. Peters, F.F. de Biani, J.W. Bats, E. Herdtweck, P. Zanello, M. Wagner,
Inorg. Chem. 40 (2001) 4928.
[
[
14] R. Han, G. Parkin, Inorg. Chem. 31 (1992) 983.
15] (a) J. Bacon, J.W. Quail, R.J. Gillespie, Can. J. Chem. 41 (1963) 3063;
(b) H. Braunschweig, R.D. Dewhurst, Dalton Trans. 40 (2011) 549;
(c) A. Amgoune, D. Bourissou, Chem. Commun. 47 (2011) 859;
(d) G. Parkin, Organometallics 25 (2006) 4744.
(
(
(
(
b) M. Suzuki, R. Kubo, Mol. Phys. 7 (1963) 201;
c) P. Kofod, J. Magn. Reson. Ser. A 119 (1996) 219;
d) A. Gryff-Keller, Bull. Pol. Acad. Sci. Chem. 46 (1998) 105;
[30] V.D. de Castro, G.M. de Lima, C.A.L. Filgueiras, M.T.P. Gambardella, J. Mol.
Struct. 609 (2002) 199.
[31] M. Wenger, T. Armbruster, Eur. J. Miner. 3 (1991) 387.
[32] J.H.N. Buttery, N.C. Plackett, B.W. Skelton, C.R. Whitaker, A.H. White, Z. Anorg.
Allg. Chem. 632 (2006) 1856.
e) G.M. Whitesides, H.L. Mitchell, J. Am. Chem. Soc. 91 (1969) 2245.
7
[
16] For other reports of Li NMR spectroscopic chemical shift data, see:
(
a) A.G. Avent, D. Bonafoux, C. Eaborn, M.S. Hill, P.B. Hitchcock, J.D. Smith, J.
Chem. Soc., Dalton Trans. (2000) 2183;
(
(
(
b) M. Schmeisser, A. Zahl, A. Scheurer, R. Puchta, R. van Eldik, Z. Naturforsch.
B) 65 (2010) 405;
c) M. Schmeisser, F.W. Heinemann, P. Illner, R. Puchta, A. Zahl, R. van Eldik,
[33] For another example trigonal monopyramidal coordination in a polynuclear
compound, see: Z.B. Duan, V.G. Young, J.G. Verkade, Inorg. Chem. 34 (1995)
2179.
Inorg. Chem. 50 (2011) 6685;
d) E. Pasgreta, R. Puchta, M. Galle, N.V.E. Hommes, A. Zahl, R. Van Eldik, J. Incl.
Phenom. Macrocycl. Chem. 58 (2007) 81;
e) E. Pasgreta, R. Puchta, A. Zahl, R. van Eldik, Eur. J. Inorg. Chem. (2007)
815;
[34] G. Fraenkel, A. Chow, R. Fleischer, H. Liu, J. Am. Chem. Soc. 126 (2004) 3983.
[35] S. Aharonovich, M. Botoshanski, M.S. Eisen, Inorg. Chem. 48 (2009) 5269.
[36] H.E. Gottlieb, V. Kotlyar, A. Nudelman, J. Org. Chem. 62 (1997) 7512.
[37] G.R. Fulmer, A.J.M. Miller, N.H. Sherden, H.E. Gottlieb, A. Nudelman, B.M. Stoltz,
J.E. Bercaw, K.I. Goldberg, Organometallics 29 (2010) 2176.
(
(
1
(
(
(
(
(
f) E. Pasgreta, R. Puchta, A. Zahl, R. van Eldik, Eur. J. Inorg. Chem. (2007) 3067;
g) A. Shirai, Y. Ikeda, Inorg. Chem. 50 (2011) 1619;
h) K.J. Kolonko, M.M. Biddle, I.A. Guzei, H.J. Reich, J. Am. Chem. Soc. 131
2009) 11525;
[39] W.L. Smith, J. Chem. Educ. 54 (1977) 469.
[40] (a) R.K. Harris, E.D. Becker, S.M.C. De Menezes, R. Goodfellow, P. Granger, Pure
Appl. Chem. 73 (2001) 1795;
Res.
(2007),
i) H.J. Reich, D.P. Green, M.A. Medina, W.S. Goldenberg, B.O. Gudmundsson,
R.R. Dykstra, N.H. Phillips, J. Am. Chem. Soc. 120 (1998) 7201.
(b) R.K. Harris, E.D. Becker, S.M.C. De Menezes, P. Granger, R.E. Hoffman, K.W.
Zilm, Pure Appl. Chem. 80 (2008) 59.
[41] (a) G.M. Sheldrick, SHELXTL, An Integrated System for Solving, Refining and
Displaying Crystal Structures from Diffraction Data, University of Göttingen,
Göttingen, Federal Republic of Germany, 1981;
0
RR
17] For 1 B NMR spectroscopic studies on [Tp ]M derivatives, see Ref. [6b] and:
a) D. Sanz, R.M. Claramunt, J. Glaser, S. Trofimenko, J. Elguero, Magn. Reson.
Chem. 34 (1996) 843;
b) I. Alkorta, J. Elguero, R.M. Claramunt, C. Lopez, D. Sanz, Heterocycl.
1
[
(
(
Commun. 16 (2010) 261.
(b) G.M. Sheldrick, Acta Crystallogr., Sect. A 64 (2008) 112.
[42] JAGUAR 7.5, Schrödinger, LLC, New York, NY, 2008.
[43] (a) A.D. Becke, J. Chem. Phys. 98 (1993) 5648;
[
[
18] V. Galasso, G. Fronzoni, J. Chem. Phys. 85 (1986) 5200.
0
19] For 1 N NMR studies on [Tp ]M derivatives, see Refs. [6b,17a,b] and: R.M.
Claramunt, D. Sanz, M.D. Santa Maria, J. Elguero, S. Trofimenko, J. Organomet.
Chem. 689 (2004) 463.
5
R,R
(b) A.D. Becke, Phys. Rev. A 38 (1988) 3098;
(c) C.T. Lee, W.T. Yang, R.G. Parr, Phys. Rev. B 37 (1988) 785;
(d) S.H. Vosko, L. Wilk, M. Nusair, Can. J. Phys. 58 (1980) 1200;
(e) J.C. Slater, Quantum Theory of Molecules and Solids, The Self-Consistent
Field for Molecules and Solids, vol. 4, McGraw-Hill, New York, 1974.
[44] (a) P.J. Hay, W.R. Wadt, J. Chem. Phys. 82 (1985) 270;
(b) W.R. Wadt, P.J. Hay, J. Chem. Phys. 82 (1985) 284;
(c) P.J. Hay, W.R. Wadt, J. Chem. Phys. 82 (1985) 299.
2
2
Me
2
[
20] The dimethylpyrazole adduct [TpMe ]Li(pzMe H)ꢀ(pz H) also exhibits
hydrogen bonding to an additional pyrazole moiety. See: L. Hernandez, S.
Taboada, L. d’Ornelas, T. Gonzalez, R. Atencio, Acta Crystallogr., Sect. E. Struct
Rep. Online 60 (2004) M979.
[
21]
s
4
= [360 ꢁ (
L. Yang, D.R. Powell, R.P.. Houser, Dalton Trans. (2007) 955.
22] G. Zhu, G. Parkin, Inorg. Chem. 44 (2005) 9637.
a + b)]/141, where a + b is the sum of the two largest angles. See:
[
[45] R. Karlsson, J. Chem. Eng. Data 18 (1973) 290.