Ammonia & N-Donor Ligands
Donald A. House
University of Canterbury, Christchurch, and Massey University, Albany, New Zealand
Search for more papers by this authorDonald A. House
University of Canterbury, Christchurch, and Massey University, Albany, New Zealand
Search for more papers by this authorAbstract
The coordination chemistry of nonmacrocyclic ligands containing only N, C, and H atoms is surveyed. Such ligands include ammonia and linear polyamines as well as heterocyclic N-compounds and catenated N-systems. Among the topics discussed are N-ligand synthesis, metal–N bond formation, reactions of coordinated N-donor ligands, and the utilization of metal–N complexes. Structural and theoretical aspects include the consideration of metal–N stability constants, hard-acid soft-base concepts, inorganic reaction mechanisms, molecular mechanics, chelate ring stereochemistry, chirality, and supramolecular chemistry.
Further Reading
- E. C. Constable, Adv. Inorg. Chem., 1989, 34, 1.
- S. Trofimenko, Prog. Inorg. Chem., 1986, 34, 116.
References
- 3 G. J. Leigh, Nomenclature of Inorganic Chemistry, Blackwell Scientific (IUPAC), Oxford, 1990, Tables I-10.5, X, p. 160.
- 4 D. S. Moore and S. D. Robinson, Adv. Inorg. Chem. Radiochem., 1986, 30, 1.
- 5 D. S. Moore and S. D. Robinson, Adv. Inorg. Chem., 1988, 32, 171.
- 6 F. A. Cotton and G. Wilkinson, Advanced Inorganic Chemistry, 5th edn., Wiley, New York, 1988.
- 7 G. Wilkinson ed., Comprehensive Coordination Chemistry, Pergamon Press, Oxford, 1987, Vol. 2, p. 715.
- 8 J. L. Burmeister, in The Chemistry and Biochemistry of Thiocyanic Acid, ed. A. A. Newman, Academic Press, New York, 1975.
- 9 L. D. Pettit and K. J. Powell, SC-Database: Stability Constant Database: IUPAC, Academic Software, 2001.
- 10 C. S. Garner and D. A. House, Transition Met. Chem. (N. Y.), 1970, 6, 59.
- 11 J. C. Chang, J. Indian Chem. Soc., 1977, 54, 88.
- 12 R. D. Hancock and A. E. Martell, Comments Inorg. Chem., 1988, 6, 237.
- 13
R. D. Hancock,
J. Chem. Educ.,
1992,
68,
615.
10.1021/ed069p615 Google Scholar
- 14 R. G. Pearson, J. Chem. Educ., 1968, 45, 581.
- 15 M. Micheloni, Comments Inorg. Chem., 1988, 8, 79.
- 16 D. A. House, Coord. Chem. Rev., 1977, 23, 223.
- 17 E. Ahmed, C. Chatterjee, C. J. Cooksey, M. L. Tobe, G. Williams, and M. Humanes, J. Chem. Soc., Dalton Trans., 1989, 645.
- 18 J. Dickie, BSc. Hons. Project, School of Chemistry, Australian Defence Force Academy, Canberra, 1995.
- 19 D. A. House, Comments Inorg Chem., 1977, 19, 327.
- 20 G. R. Brubaker, D. P. Schaefer, J. H. Worrell, and J. I. Legg, Coord. Chem. Rev., 1971, 7, 161.
- 21 L. Spialter and J. A. Pappalardo, The Acyclic Aliphatic Tertiary Amines, Macmillan, New York, 1965.
- 22 D. A. House, Inorg. Chim. Acta, 1986, 121, 167.
- 23 R. M. Hartshorn and D. A. House, J. Chem. Soc., Dalton Trans., 1998, 2577.
- 24 D. A. House, Coord. Chem. Rev., 1992, 114, 249.
- 25 J. E. Sarneski, A. T. McPhail, K. D. Onan, L. E. Erikson, and C. N. Reilley, J. Am. Chem. Soc., 1977, 99, 7376.
- 26 R. J. Geue, T. W. Hambley, J. Mac. B. Harrowfield, A. M. Sargeson, and M. R. Snow, J. Am. Chem. Soc., 1984, 106, 5478.
- 27 P. Newman, Optical Resolution Procedures for Chiral Compounds, Optical Resolution Information Center, Manhattan College, Riverdale, NY, 1978, Vol. 1.
- 28 C. Piguet, G. Bernardinelli, B. Bocquet, A. Quattropani, and A. F. Williams, J. Am. Chem. Soc., 1992, 114, 7440.
- 29 K. Bernauer and F. Gretillat, Helv. Chim. Acta, 1989, 72, 477.
- 30 D. Ginsberg, Concerning Amines, Pergamon Press, Oxford, 1967.
- 31 C. Caldarera, V. Zappia, and U. Bachrach eds, Advances in Polyamine Research, Raven Press, New York, 1978–1983.
- 32 P. R. Mitchell, Method. Chim., 1976, 8, 307.
- 33 S. Utsuno, Y. Sakai, Y. Yoshikawa, and H. Yamatera, J. Am. Chem. Soc., 1980, 102, 6903.
- 34 H. Nakazawa and H. Yoneda, J. Chromatog., 1978, 160, 89.
- 35 G. H. Searle, S. F. Lincoln, S. G. Teague, and D. G. Rowe, Aust. J. Chem., 1979, 32, 519.
- 36 G. H. Searle, Aust. J. Chem., 1980, 33, 2159.
- 37 P. Hendry and A. Ludi, Adv. Inorg. Chem., 1990, 35, 117.
- 38 P. V. Bernhardt and P. Comba, Inorg. Chem., 1992, 31, 2638.
- 39 P. Comba and T. W. Hambley, Molecular Modeling of Inorganic Compounds, VCH, Weinheim, 1995.
- 40
R. D. Hancock,
Prog. Inorg. Chem.,
1988,
37,
187.
10.1002/9780470166383.ch4 Google Scholar
- 41 F. M. Lappert, A. R. Sanger, R. C. Schrivaster, and P. P. Power, Metal and Metalloidal Amides, Wiley, New York, 1979.
- 42 M. H. Chisholm and I. P. Rothwell, in Comprehensive Coordination Chemistry, ed. G. Wilkinson, Pergamon Press, Oxford, 1987, Vol. 2, p. 161.
- 43 R. C. Mehorta, in Comprehensive Coordination Chemistry, ed. G. Wilkinson, Pergamon Press, Oxford, 1987, Vol. 2, p. 269.
- 44 D. A. House, in Comprehensive Coordination Chemistry, ed. G. Wilkinson, Pergamon Press, Oxford, 1987, Vol. 2, p. 23.
- 45 W. L. Jolly, Synthetic Inorganic Chemistry, Prentice Hall, New York, 1960.
- 46 K. Beveridge, G. W. Bushnell, and A. D. Kirk, Acta Crystallogr., Sect. C, 1985, 41, 899.
- 47 S. Balt and A. Jelsma, Inorg. Chem., 1981, 20, 733.
- 48 J. W. Mellor, Comprehensive Treatise of Inorganic and Theoretical Chemistry, Longmans, London, 1931.
- 49 W. S. Glaunsinger, J. Phys. Chem., 1980, 84, 1163.
- 50 Y. Pauleau, J. J. Hantzpergue, and J. C. Remy, Bull. Soc. Chim. Fr., 1978, 246.
- 51 P. C. Ford, Coord. Chem. Rev., 1970, 5, 75.
- 52 H. Taube, Pure Appl. Chem., 1979, 51, 901.
- 53 D. Waysbort and G. Navon, Inorg. Chem., 1979, 18, 9.
- 54 G. G. Schlessinger, Inorganic Laboratory Preparations, Chem. Pub. Co., New York, 1962.
- 55 G. Glidewell, J. Coord. Chem., 1977, 6, 189.
- 56 S. Fallab and P. R. Mitchell, Adv. Inorg. Bioinorg. Mech., 1984, 3, 111.
- 57 S. E. Miller and D. A. House, Inorg. Chim. Acta, 1989, 161, 131.
- 58 S. E. Miller and D. A. House, Inorg. Chim. Acta, 1989, 166, 189.
- 59 S. E. Miller and D. A. House, Inorg. Chim. Acta, 1990, 173, 53.
- 60 S. E. Miller and D. A. House, Inorg. Chim. Acta, 1991, 187, 125.
- 61 S. E. Miller, Huo. Wen, D. A. House, and W. T. Robinson, Inorg. Chim. Acta, 1991, 184, 111.
- 62 S. E. Miller, K. J. Gerard, and D. A. House, Inorg. Chim. Acta, 1991, 190, 135.
- 63 E. Koubek and D. A. House, Inorg. Chim. Acta, 1992, 191, 103.
- 64 M. Kojima, A. Sakurai, M. Murata, K. Nakajima, S. Yashino, and nd. Y. Yoshikawa, J. Coord. Chem., 1997, 42, 95.
- 65 D. A. Thompson, J. Coord. Chem., 1991, 24, 261.
- 66 M. M. Muir and H. M. Torres, Inorg. Chem., 1992, 31, 4160.
- 67 J. Castro, P. P. Lourido, A. Sousa-Pedrares, E. Labisbal, M. Carabel, and J. A. Garcia-Vazquez, Acta. Crystallogr., 2002, 58C, m65.
- 68 A. M. Mills, K. Flinzner, A. F. Stassen, J. G. Haasnoot, and A. L. Spek, Acta Crystallogr., 2002, 58C, m243.
- 69 T. Otieno, J. R. Blanton, M. J. Hatfield, S. L. Asher, and S. Parkin, Acta Crystallogr., 2002, 58C, m182.
- 70 R. A. Jones ed., Heterocyclic Compounds, Wiley, New York, 1990, Vol. 48, Part 1.
- 71 S. R. A. Kkan, I. Guzman-Jimenez, K. H. Whitmire, and A. R. Kohkhar, Polyhedron, 2000, 19, 975.
- 72 J. Chatt, J. R. Dillworth, and R. L. Richards, Chem. Rev., 1978, 78, 589.
- 73
R. A. Henderson,
G. J. Leigh, and
C. J. Pickett,
Adv. Inorg. Chem. Radiochem.,
1983,
27,
198.
10.1016/S0898-8838(08)60108-7 Google Scholar
- 74 H. M. Colquhoun, Acc. Chem. Res., 1984, 17, 23.
- 75 G. J. Leigh, Transition Met. Chem., 1986, 11, 118.
- 76
M. Hidai and
Y. Mizobe, in
Reactions of Coordinated Ligands, ed.
P. S. Braterman,
Plenum Press,
New York,
1989,
Vol. 2, p.
53.
10.1007/978-1-4613-0755-6_2 Google Scholar
- 77 J. E. Fergusson and J. L. Love, Rev. Pure Appl. Chem., 1970, 20, 33.
- 78 K. Kohata, T. Fukuyama, and K. Kuchitsu, J. Phys. Chem., 1982, 86, 602.
- 79 G. Stedman, Adv. Inorg. Chem. Radiochem., 1979, 22, 114.
- 80 B. F. Johnston, B. L. Haymore, and J. R. Dillworth, in Comprehensive Coordination Chemistry, ed. G. Wilkinson, Pergamon Press, Oxford, 1987, Vol. 2, p. 99.
- 81 A. D. Ryabov, Chem. Rev., 1990, 90, 403.
- 82 M. P. Doyle, Acc. Chem. Res., 1986, 19, 348.
- 83 M. P. Suh, S.-G. Kang, V. L. Goedken, and S.-H. Park, Inorg. Chem., 1991, 30, 365.
- 84 Huo. Wen, S. E. Miller, D. A. House, V. McKee, and W. T. Robinson, Inorg. Chim. Acta, 1992, 193, 77.
- 85 D. A. House, V. McKee, and W. T. Robinson, Inorg. Chim. Acta, 1989, 157, 15.
- 86 D. A. House and P. J. Steel, Inorg. Chim. Acta, 1999, 288/1, 53.
- 87 J. Ellermeier, R. Stahler, and W. Bensch, Acta Crystallogr., 2002, 58C, m70.
- 88 R. Fanshawe, A. Mobinikhaledi, C. R. Clark, and A. G. Blackburn, Inorg. Chim. Acta, 2000, 307, 26.
- 89 K. F. Purcell and J. C. Kotz, Inorganic Chemistry, W.B. Saunders, 1977, p. 636; G. J. Leigh, Nomenclature of Inorganic Chemistry, Blackwell Scientific (IUPAC), Oxford, 1990 Tables I-10.5, X, p. 184.
- 90 G. B. Kauffman and E. V. Lindley, J. Chem. Educ., 1974, 51, 424.
- 91 I. Bernal, J. Chem. Educ., 1992, 69, 468.
- 92 H. Chun, S. S. Massoud, R. Wen, and I. Bernal, Polyhedron, 1999, 18, 3647.
- 93 M. Abdou, C. Krathy, and G. Uray, Monatsh. Chem., 1990, 121, 1039.
- 94 S. T. Chan, C. I. Dickie, L. T. Ellis, V. P. Monk, B. A. Messerle, and T. W. Hambley, J. Chem. Soc., Dalton Trans., 2001, 2769.
- 95 R. Saito and Y. Kidani, Chem. Lett., 1976, 123.
- 96 K. J. Gerard, J. Morgan, P. J. Steel, and D. A. House, Inorg. Chim. Acta, 1997, 260, 27.
- 97 B.-J. Kim, Y.-M. Lee, E. H. Kim, S. K. Kang, and S.-N. Choi, Acta Crystallogr., 2002, 58C, 361.
- 98 J. Reedijk, in Comprehensive Coordination Chemistry, ed. G. Wilkinson, Pergamon Press, Oxford, 1987, Vol. 2, p. 73.
- 99 P. J. Steel, Coord. Chem. Rev., 1990, 106, 227.
- 100 E. C. Constable and P. J. Steel, Coord. Chem. Rev., 1989, 93, 205.
- 101 C. Kaes, A. Katz, and M. W. Hosseini, Chem. Rev., 2000, 100, 3552.
- 102 G. Chelucci and R. P. Thummel, Chem. Rev., 2002, 102, 3129.
- 103 E. Krause and J. Ferguson, Prog. Inorg. Chem., 1989, 37, 293.
- 104 L. E. Foster, Chem. Rev., 1990, 90, 331.
- 105 R. Mukherjee, Coord. Chem. Rev., 2000, 203, 151.
- 106 D. A. House, P. J. Steel, and A. A. Watson, Aust. J. Chem., 1986, 39, 1525.
- 107 K. Vrieze and G. van Koten, in Comprehensive Coordination Chemistry, ed. G. Wilkinson, Pergamon Press, Oxford, 1987, Vol. 2, p. 189.
- 108 A. N. Golub, H. Kohler, and V. V. Skopenko eds, Chemistry of the Pseudohalides, Elsevier, Amsterdam, NY, 1986.
- 109 G. A. Lawrance, Adv. Inorg. Chem., 1989, 34, 145.
- 110 R. W. Hay and F. M. McLaren, Transition Met. Chem., 1999, 24, 398.
- 111 A. Hazell, C. J. McKenzie, and L. P. Nielsen, Polyhedron, 2000, 19, 1333.
- 112 D. R. Morris and L. Marton eds, Polyamines in Biology and Medicine, Dekker, New York, 1981.
- 113 C. W. Tabor and H. Tabor, Ann. Rev. Biochem., 1984, 53, 749.
- 114 C. Navarro-Ranninger, F. Zamora, J. M. Pérez, I. López-Solera, S. Martinez-Carrera, J. R. Masaguer, and C. Alonso, J. Inorg. Biochem., 1992, 47, 267.
- 115 M. Harlerow and C. A. Kilner, Acta Crystallogr., 2002, 58C, m424.
- 116 K. H. Kim, Acta Crystallogr., 2000, 56C, e557.
- 117 M. Scarplline, Acta Crystallogr., 2001, 57C, 356.
- 118 R. Balamurugan, M. Palaniandavar, and R. S. Gopalan, Inorg. Chem., 2001, 40, 2246.
- 119 G. Muller, J.-C. G. Bunzli, K. J. Schenk, C. Piguet, and G. Hopfgartner, Inorg. Chem., 2001, 40, 2642.
- 120 C. W. Glynn and M. M. Turnbull, Inorg. Chim. Acta, 2002, 332, 92.
- 121 G. A. van Albade, I. Mutikainen, U. Turpeinen, and J. Reedijk, Acta Crystallogr., 2002, 58C, m179.
- 122 D. L. Reger, C. A. Little, M. D. Smith, A. L. Rheingold, L. M. Liable-Sands, G. P. A. Yap, and I. A. Guzie, Inorg. Chem., 2002, 41, 19.
- 123 D. Martini, M. Pellei, C. Pettinari, B. W. Skelton, and A. H. White, Inorg. Chim. Acta, 2002, 333, 72.
- 124 W. Yang, L. Chen, and S. Wang, Inorg. Chem., 2001, 40, 507.
- 125 X.-H. Bu, M. Du, L. Zhang, Z.-L. Shang, R.-H. Zangand, and M. Shionoya, J. Chem. Soc., Dalton Trans., 2001, 729.
- 126 M.-H. Choi, B. J. Kim, I.-C. Kim, S.-H. Kim, Y. Kim, J. M. Harrowfield, M.-K. Lee, M. Mocerino, E. Rukmini, B. W. Skelton, and A. H. White, J. Chem. Soc., Dalton Trans., 2001, 707.
- 127 B. Fabins, R. J. Geue, R. G. Hazell, W. G. Jackson, F. K. Larsen, C. J. Qin, and A. M. Sargeson, J. Chem. Soc., Dalton Trans., 1999, 3961.
- 128 J. M. Harrowfield, G. H. Jang, Y. Kim, P. Thuery, and J. Vicens, J. Chem. Soc., Dalton Trans., 2002, 1241.
- 129 E. C. Constable, Adv. Inorg. Chem. Radiochem., 1986, 30, 69.
- 130 E. C. Constable, Tetrahedron, 1992, 48, 10013.
- 131 S. G. Zipp, A. P. Zipp, and S. K. Madan, J. Indian Chem. Soc., 1977, 54, 149.
- 132 A. Dossing, A. Hazell, and H. Toftlund, Acta Chem. Scand., 1996, 50, 95.
- 133 F. C. Sanudo, A. A. Grillo, M. J. Knapp, J. C. Bollinger, J. C. Huffman, D. N. Hendrickson, and G. Christou, Inorg. Chem., 2002, 41, 2441.
- 134 D. A. Buckingham, W. G. Jackson, P. A. Marzilli, and A. M. Sargeson, Aust. J. Chem., 1999, 52, 185.
- 135 J. M. W. Browne, J. Wikaira, and R. M. Hartshorn, J. Chem. Soc., Dalton Trans., 2001, 3513.
- 136 M. D. Vaira, F. Mani, and P. Stoppioni, Inorg. Chim. Acta, 2000, 303, 61.
- 137 F. V. Rybak-Akimova, A. Y. Nazarenko, L. Chen, P. W. Krieger, A. M. Herrera, V. V. Tarasov, and P. D. Robinson, Inorg. Chim. Acta, 2001, 324, 1.
- 138 A. Grohmann and F. Knoch, Inorg. Chem., 1996, 35, 7932.
- 139 C. Jubert, A. Mohomadou, E. Guillon, and J.-P. Barbier, Polyhedron, 2000, 19, 1447.
- 140 S.-D. Kim, J.-W. Kim, and W.-S. Jung, Polyhedron, 1998, 17, 1223.
- 141
D. da Luz,
C. V. Franco,
I. Vencato,
A. Neves, and
Y. P. Mascarenhas,
J. Coord. Chem.,
1992,
26,
269.
10.1080/00958979209407929 Google Scholar
- 142 G. Park, N. Ye, R. D. Rogers, M. W. Brechbiel, and R. P. Planalp, Polyhedron, 2000, 19, 1155.
- 143 T. Mashiko and D. Dolphin, in Comprehensive Coordination Chemistry, ed. G. Wilkinson, Pergamon Press, Oxford, 1987, Vol. 2, p. 813.
- 144 P. Ray, Chem. Rev., 1961, 61, 313.
- 145 P. Ray, Inorg. Synth., 1960, 6, 75.
- 146 H. Sigel, N. A. Corfu, L.-N. Ji, and R. B. Martin, Comments Inorg. Chem., 1992, 13, 35.
- 147 A. E. Martell and M. Calvin, Chemistry of the Metal Chelate Compounds, Prentice-Hall, New York, 1956, p. 140.
- 148 P. Ferruti and R. Barbucci, Adv. Polym. Sci., 1984, 58, 155.
- 149 N. F. Curtis, in Comprehensive Coordination Chemistry, ed. G. Wilkinson, Pergamon Press, Oxford, 1987, Vol. 2, p. 899.
- 150 N. F. Curtis and O. P. Gladkikh, Aust. J. Chem., 2000, 53, 597.
- 151 A. Riesen, M. Zehnder, and D. A. House, Inorg. Chim. Acta, 1986, 113, 163.
- 152
B. N. Storhoff and
H. C. Lewis,
Coord. Chem. Rev.,
1972,
23,
1.
10.1016/S0010-8545(00)80329-X Google Scholar
- 153 H. Endres, in Comprehensive Coordination Chemistry, ed. G. Wilkinson, Pergamon Press, Oxford, 1987, Vol. 2, p. 261.
- 154 D. Yang and D. A. House, Polyhedron, 1983, 2, 1267.
- 155 F. Swiegers and T. J. Malefetse, Chem. Rev., 2000, 100, 3483; Coord. Chem. Rev., 2002, 225, 91.
- 156 S. Leininger, B. Olenyuk, and P. J. Stang, Chem. Rev., 2000, 100, 853.
- 157
B. J. Holliday and
C. A. Mirkin,
Angew. Chem., Int. Ed. Engl.,
2001,
40,
2022.
10.1002/1521-3773(20010601)40:11<2022::AID-ANIE2022>3.0.CO;2-D CAS PubMed Web of Science® Google Scholar
- 158 C. V. K. Sharma, J. Chem. Educ., 2001, 78, 617.
- 159 P. J. Steel, Chem. New Zealand, 2003, 67, 57.
- 160 G. Dong, D. Chun-ying, F. Chan-jie, and M. Qing-jin, J. Chem. Soc., Dalton Trans., 2002, 834.
- 161 A. Kunze, R. Gleiter, F. Rominger, and T. Oeser, J. Chem. Soc., Dalton Trans., 2002, 1217.
- 162 D. L. Caulder and K. N. Raymond, J. Chem. Soc., Dalton Trans., 1999, 1185.
- 163 M. Albrecht, Chem. Rev., 2001, 101, 3457.
- 164 H.-K. Liu, J. Hu, T.-W. Wang, X.-L. Yu, J. Liu, and B. Kang, J. Chem. Soc., Dalton Trans., 2001, 3534.
- 165 C. He, L.-Y. Wang, Z.-M. Wang, Y. Liu, C.-S. Liao, and C.-H. Yan, J. Chem. Soc., Dalton Trans., 2002, 134.