Crystal and Molecular Structure of the [6-Deoxy-6-[(2-(4-imidazolyl)ethyl)amino]cyclomaltoheptaose]copper(II) Ternary Complex with L-Tryptophanate. Role of Weak Forces in the Chiral Recognition Process Assisted by a Metallocyclodextrin (314 views)
Inorg Chem (ISSN: 0020-1669, 1520-510x, 1520-510xelectronic), 1996 Jul 17; 35(15): 4497-4504.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 2.736, 5-year impact factor: 4.04
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-0000540729&partnerID=40&md5=228aefc4c670d605a00a0d5de9f03ba2
Keywords: Not available.
Affiliations:
Dipartimento di Scienze Chimiche, Università di Catania, 95125 Catania, Italy
Dipartimento di Chimica, Università della Basilicata, via N. Sauro 85, 85100 Potenza, Italy
Facoltà di Scienze Ambientali, Seconda Università di Napoli, via Arena 22, 81100 Caserta, Italy
Ist. Per Stud. S. N. I. A. C. F., CNR, v.le A. Doria 6, 95125, Italy
Facolt di Scienze Ambientali, Seconda Universit di Napoli, via Arena 22, 81100 Caserta, Italy
References:
Righy, M., Smith, E.B., Wakeham, W.A., Maitland, G.C., (1986) The Forces between Molecules, , Oxford Science Publications, Clarendon Press: Oxford, U.
Tanford, C., (1980) The Hydrophobic Effect, , Wiley: NewYork
Sinanoglu, O., (1980) Int. J. Quantum Chem., 18, p. 381
Breslow, R., (1990) Pure Appl. Chem., 62, p. 1859
Lehn, J.-M., (1990) Angew. Chem., Int. Ed. Engl., 29, p. 1304
Ikeura, Y., Kurihara, K., Kunitake, T., (1991) J. Am. Chem. Soc., 113, p. 7342
Rebek Jr., J., (1990) Angew. Chem., Int. Ed. Engl., 29, p. 245
Cooper, A., MacNicol, D.D., (1978) J. Am. Chem. Soc., Perkin Trans. 2, p. 760
Brown, S.E., Coates, J.H., Lincoln, S.F., Coghlan, D.R., Easton, C.J., (1991) J. Chem. Soc., Faraday Trans., 87, p. 2699
Colquham, I.J., Goodfellow, B.J., (1994) J. Chem. Soc., Perkin Trans. 2, p. 1803
Word, T.J., Armstrong, D.W., (1986) J. Liq. Chromatogr., 9, p. 407
Lipkowitz, K.B., Raghthama, S., Yang, J., (1992) J. Am. Chem. Soc., 114, p. 1554
Impellizzeri, G., Maccarrone, G., Rizzarelli, E., Vecchio, G., Corradini, R., Marchelli, R., (1991) Angew. Chem., Int. Ed. Engl., 30, p. 1348
Theophanides, T., Eds.
Kluwer: Dordrecht, The Netherlands
Cucinotta, V., D'Alessandro, F., Impellizzeri, G., Vecchio, G., (1992) J. Chem. Soc., Chem. Commun., p. 1743
Bonomo, R.P., Cucinotta, V., D'Alessandro, F., Impellizzeri, G., Maccarrone, G., Rizzarelli, E., Vecchio, G., (1993) J. Inclusion Phenom., 15, p. 167
Corradini, R., Dossena, A., Impellizzeri, G., Maccarrone, G., Marchelli, R., Rizzarelli, E., Sartor, G., Vecchio, G., (1994) J. Am. Chem. Soc., 116, p. 10267
Altomare, A., Burla, M.C., Camalli, M., Cascarano, G., Giacovazzo, C., Gugliardi, A., Polidori, G., (1994) J. Appl. Crystallogr., 27, p. 435
(1979) Enraf-Nonius Structure Determination Package, , Enraf-Nonius: Delft, The Netherlands
Cromer, D.T., Waber, J.T., (1984) International Tables for X-Ray Crystallography, 4. , The Kynoch Press: Birminghan, England, Table 2.2B
Bonomo, R.P., Riggi, F., (1982) Chem. Phys. Lett., 93, p. 99
Pilbrow, J.R., Winfield, M.E., (1973) Mol. Phys., 26, p. 1073
Lindner, K., Saenger, W., (1982) Carbohydr. Res., 99, p. 103
Di Blasio, B., Pavone, V., Nastri, F., Isernia, C., Saviano, M., Pedone, C., Cucinotta, V., Vecchio, G., (1992) Proc. Natl. Acad. Sci. U.S.A., 89, p. 7218
Kamitori, S., Hirotsu, K., Fujita, K., Yamamura, H., Imoto, T., Tabushi, I., (1987) J. Chem. Soc., Perkin Trans. 2, p. 10
Zabel, V., Saenger, W., Maso, S.A., (1986) J. Am. Chem. Soc, 108, p. 3663
Hamilton, T.A., Chen, L.Y., (1988) J. Am. Chem. Soc., 110, p. 4379
Pajunen, A., Pajunen, S., (1982) Acta Crystalhgr., B38, p. 3093
Van Der Helm, D., Tatsch, C.E., (1972) Acta Crystallogr., B28, p. 2307
Franks, W.A., Van Der Helm, D., (1970) Acta Crystallogr., B27, p. 1299
Hursthouse, M.B., Jayaweera, S.A.A., Milburn, H., Quick, A., (1975) J. Chem. Soc., Dalton Trans., p. 2569
Yamauchi, O., Kohzuma, T., Masuda, H., Toriumi, K., Saito, K., (1989) Inorg. Chem., 28, p. 4066
Harata, K., (1988) Bull. Chem. Soc. Jpn., 61, p. 1939
Fuijwara, T., Tanaka, N., Hamada, K., Kobayashi, S., (1989) Chem. Lett., p. 1131
Amico, P., Bonomo, R.P., Calì, R., Cucinotta, V., Daniele, P.G., Ostacoli, G., Rizzarelli, E., (1989) Inorg. Chem., 28, p. 3555
Arena, G., Bonomo, R.P., Casella, L., Gullotti, M., Impellizzeri, G., Maccarrone, G., Rizzarelli, E., (1991) J. Chem. Soc., Dalton Trans., p. 3203
Bonomo, R.P., Bonsignore, F., Conte, E., Impellizzeri, G., Pappalardo, G., Purrello, R., Rizzarelli, E., (1993) J. Chem. Soc., Dalton Trans., p. 1295
Borghesani, G., Pulidori, F., Purrello, R., Remelli, M., Rizzarelli, E., (1990) J. Chem. Soc., Dalton Trans., p. 2095
Pettit, L.D., Hefford, R.J.W., (1979) Metal Ions in Biological Systems, 9, p. 174. , Sigel, H., Ed.
Marcel Dekker: New York
Lehn, J. -M., (1990) Angew. Chem., Int. Ed. Engl., 29, p. 1304
Brown, S. E., Coates, J. H., Lincoln, S. F., Coghlan, D. R., Easton, C. J., (1991) J. Chem. Soc., Faraday Trans., 87, p. 2699
Colquham, I. J., Goodfellow, B. J., (1994) J. Chem. Soc., Perkin Trans. 2, p. 1803
Word, T. J., Armstrong, D. W., (1986) J. Liq. Chromatogr., 9, p. 407
Lipkowitz, K. B., Raghthama, S., Yang, J., (1992) J. Am. Chem. Soc., 114, p. 1554
Bonomo, R. P., Cucinotta, V., D'Alessandro, F., Impellizzeri, G., Maccarrone, G., Rizzarelli, E., Vecchio, G., (1993) J. Inclusion Phenom., 15, p. 167
(1979) Enraf-Nonius Structure Determination Package, , Enraf-Nonius: Delft, The Netherlands
Cromer, D. T., Waber, J. T., (1984) International Tables for X-Ray Crystallography, 4. , The Kynoch Press: Birminghan, England, Table 2. 2B
Bonomo, R. P., Riggi, F., (1982) Chem. Phys. Lett., 93, p. 99
Pilbrow, J. R., Winfield, M. E., (1973) Mol. Phys., 26, p. 1073
Hamilton, T. A., Chen, L. Y., (1988) J. Am. Chem. Soc., 110, p. 4379
Franks, W. A., Van Der Helm, D., (1970) Acta Crystallogr., B27, p. 1299
Hursthouse, M. B., Jayaweera, S. A. A., Milburn, H., Quick, A., (1975) J. Chem. Soc., Dalton Trans., p. 2569
Bonomo, R. P., Bonsignore, F., Conte, E., Impellizzeri, G., Pappalardo, G., Purrello, R., Rizzarelli, E., (1993) J. Chem. Soc., Dalton Trans., p. 1295
Pettit, L. D., Hefford, R. J. W., (1979) Metal Ions in Biological Systems, 9, p. 174. , Sigel, H., Ed.
Inorg Chem (ISSN: 0020-1669, 1520-510x, 1520-510xelectronic), 1996 Jul 17; 35(15): 4497-4504.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 2.736, 5-year impact factor: 4.04
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-0000540729&partnerID=40&md5=228aefc4c670d605a00a0d5de9f03ba2
Keywords: Not available.
Affiliations:
Dipartimento di Scienze Chimiche, Università di Catania, 95125 Catania, Italy
Dipartimento di Chimica, Università della Basilicata, via N. Sauro 85, 85100 Potenza, Italy
Facoltà di Scienze Ambientali, Seconda Università di Napoli, via Arena 22, 81100 Caserta, Italy
Ist. Per Stud. S. N. I. A. C. F., CNR, v.le A. Doria 6, 95125, Italy
Facolt di Scienze Ambientali, Seconda Universit di Napoli, via Arena 22, 81100 Caserta, Italy
References:
Righy, M., Smith, E.B., Wakeham, W.A., Maitland, G.C., (1986) The Forces between Molecules, , Oxford Science Publications, Clarendon Press: Oxford, U.
Tanford, C., (1980) The Hydrophobic Effect, , Wiley: NewYork
Sinanoglu, O., (1980) Int. J. Quantum Chem., 18, p. 381
Breslow, R., (1990) Pure Appl. Chem., 62, p. 1859
Lehn, J.-M., (1990) Angew. Chem., Int. Ed. Engl., 29, p. 1304
Ikeura, Y., Kurihara, K., Kunitake, T., (1991) J. Am. Chem. Soc., 113, p. 7342
Rebek Jr., J., (1990) Angew. Chem., Int. Ed. Engl., 29, p. 245
Cooper, A., MacNicol, D.D., (1978) J. Am. Chem. Soc., Perkin Trans. 2, p. 760
Brown, S.E., Coates, J.H., Lincoln, S.F., Coghlan, D.R., Easton, C.J., (1991) J. Chem. Soc., Faraday Trans., 87, p. 2699
Colquham, I.J., Goodfellow, B.J., (1994) J. Chem. Soc., Perkin Trans. 2, p. 1803
Word, T.J., Armstrong, D.W., (1986) J. Liq. Chromatogr., 9, p. 407
Lipkowitz, K.B., Raghthama, S., Yang, J., (1992) J. Am. Chem. Soc., 114, p. 1554
Impellizzeri, G., Maccarrone, G., Rizzarelli, E., Vecchio, G., Corradini, R., Marchelli, R., (1991) Angew. Chem., Int. Ed. Engl., 30, p. 1348
Theophanides, T., Eds.
Kluwer: Dordrecht, The Netherlands
Cucinotta, V., D'Alessandro, F., Impellizzeri, G., Vecchio, G., (1992) J. Chem. Soc., Chem. Commun., p. 1743
Bonomo, R.P., Cucinotta, V., D'Alessandro, F., Impellizzeri, G., Maccarrone, G., Rizzarelli, E., Vecchio, G., (1993) J. Inclusion Phenom., 15, p. 167
Corradini, R., Dossena, A., Impellizzeri, G., Maccarrone, G., Marchelli, R., Rizzarelli, E., Sartor, G., Vecchio, G., (1994) J. Am. Chem. Soc., 116, p. 10267
Altomare, A., Burla, M.C., Camalli, M., Cascarano, G., Giacovazzo, C., Gugliardi, A., Polidori, G., (1994) J. Appl. Crystallogr., 27, p. 435
(1979) Enraf-Nonius Structure Determination Package, , Enraf-Nonius: Delft, The Netherlands
Cromer, D.T., Waber, J.T., (1984) International Tables for X-Ray Crystallography, 4. , The Kynoch Press: Birminghan, England, Table 2.2B
Bonomo, R.P., Riggi, F., (1982) Chem. Phys. Lett., 93, p. 99
Pilbrow, J.R., Winfield, M.E., (1973) Mol. Phys., 26, p. 1073
Lindner, K., Saenger, W., (1982) Carbohydr. Res., 99, p. 103
Di Blasio, B., Pavone, V., Nastri, F., Isernia, C., Saviano, M., Pedone, C., Cucinotta, V., Vecchio, G., (1992) Proc. Natl. Acad. Sci. U.S.A., 89, p. 7218
Kamitori, S., Hirotsu, K., Fujita, K., Yamamura, H., Imoto, T., Tabushi, I., (1987) J. Chem. Soc., Perkin Trans. 2, p. 10
Zabel, V., Saenger, W., Maso, S.A., (1986) J. Am. Chem. Soc, 108, p. 3663
Hamilton, T.A., Chen, L.Y., (1988) J. Am. Chem. Soc., 110, p. 4379
Pajunen, A., Pajunen, S., (1982) Acta Crystalhgr., B38, p. 3093
Van Der Helm, D., Tatsch, C.E., (1972) Acta Crystallogr., B28, p. 2307
Franks, W.A., Van Der Helm, D., (1970) Acta Crystallogr., B27, p. 1299
Hursthouse, M.B., Jayaweera, S.A.A., Milburn, H., Quick, A., (1975) J. Chem. Soc., Dalton Trans., p. 2569
Yamauchi, O., Kohzuma, T., Masuda, H., Toriumi, K., Saito, K., (1989) Inorg. Chem., 28, p. 4066
Harata, K., (1988) Bull. Chem. Soc. Jpn., 61, p. 1939
Fuijwara, T., Tanaka, N., Hamada, K., Kobayashi, S., (1989) Chem. Lett., p. 1131
Amico, P., Bonomo, R.P., Calì, R., Cucinotta, V., Daniele, P.G., Ostacoli, G., Rizzarelli, E., (1989) Inorg. Chem., 28, p. 3555
Arena, G., Bonomo, R.P., Casella, L., Gullotti, M., Impellizzeri, G., Maccarrone, G., Rizzarelli, E., (1991) J. Chem. Soc., Dalton Trans., p. 3203
Bonomo, R.P., Bonsignore, F., Conte, E., Impellizzeri, G., Pappalardo, G., Purrello, R., Rizzarelli, E., (1993) J. Chem. Soc., Dalton Trans., p. 1295
Borghesani, G., Pulidori, F., Purrello, R., Remelli, M., Rizzarelli, E., (1990) J. Chem. Soc., Dalton Trans., p. 2095
Pettit, L.D., Hefford, R.J.W., (1979) Metal Ions in Biological Systems, 9, p. 174. , Sigel, H., Ed.
Marcel Dekker: New York
Lehn, J. -M., (1990) Angew. Chem., Int. Ed. Engl., 29, p. 1304
Brown, S. E., Coates, J. H., Lincoln, S. F., Coghlan, D. R., Easton, C. J., (1991) J. Chem. Soc., Faraday Trans., 87, p. 2699
Colquham, I. J., Goodfellow, B. J., (1994) J. Chem. Soc., Perkin Trans. 2, p. 1803
Word, T. J., Armstrong, D. W., (1986) J. Liq. Chromatogr., 9, p. 407
Lipkowitz, K. B., Raghthama, S., Yang, J., (1992) J. Am. Chem. Soc., 114, p. 1554
Bonomo, R. P., Cucinotta, V., D'Alessandro, F., Impellizzeri, G., Maccarrone, G., Rizzarelli, E., Vecchio, G., (1993) J. Inclusion Phenom., 15, p. 167
(1979) Enraf-Nonius Structure Determination Package, , Enraf-Nonius: Delft, The Netherlands
Cromer, D. T., Waber, J. T., (1984) International Tables for X-Ray Crystallography, 4. , The Kynoch Press: Birminghan, England, Table 2. 2B
Bonomo, R. P., Riggi, F., (1982) Chem. Phys. Lett., 93, p. 99
Pilbrow, J. R., Winfield, M. E., (1973) Mol. Phys., 26, p. 1073
Hamilton, T. A., Chen, L. Y., (1988) J. Am. Chem. Soc., 110, p. 4379
Franks, W. A., Van Der Helm, D., (1970) Acta Crystallogr., B27, p. 1299
Hursthouse, M. B., Jayaweera, S. A. A., Milburn, H., Quick, A., (1975) J. Chem. Soc., Dalton Trans., p. 2569
Bonomo, R. P., Bonsignore, F., Conte, E., Impellizzeri, G., Pappalardo, G., Purrello, R., Rizzarelli, E., (1993) J. Chem. Soc., Dalton Trans., p. 1295
Pettit, L. D., Hefford, R. J. W., (1979) Metal Ions in Biological Systems, 9, p. 174. , Sigel, H., Ed.
Crystal and Molecular Structure of the [6-Deoxy-6-[(2-(4-imidazolyl)ethyl)amino]cyclomaltoheptaose]copper(II) Ternary Complex with L-Tryptophanate. Role of Weak Forces in the Chiral Recognition Process Assisted by a Metallocyclodextrin
The ternary copper(II) complex of 6-deoxy-6-[(2-(4-imidazolyl)ethyl)amino]cyclomaltoheptaose (CDhm) and L-tryptophanate (L-TrpO-) was characterized by ESR and X-ray diffraction. The solid state structure of [Cu(CDhm)-(L-TrpO)]+ shows that the aromatic side chain of TrpO- is outside the cavity and that the two amino nitrogen atoms, one from the histamine molecule and one from the amino acidate, are in a cis disposition. The two amino nitrogens, the imidazole nitrogen, and the carboxylate oxygen atoms form the base of a square pyramid, which surrounds the copper(II) ion, a water molecule occupying an apical position. Atomic distances suggest for this complex that π-π and d-π interactions could occur in the solid state. Morover, the [Cu(CDhm)(L-TrpO)]+ has a self-assembled structure in which a CDhm molecule behaves as host and as guest. The imidazole and the indole ring are directed into the cavity of an adjacent CDhm molecule from the wider cyclodextrin rim, thus forming a polymeric column structure. ESR spectra were run on the copper(II) ternary complexes with L- or D-tryptophanate and L- or D-alaninate in frozen aqueous solution and on the former pair of enantiomers in the solid state, as well. While in the case of the ternary complex with L- or D-alaninate no differences are observed in their frozen solution spectra, in the case of complexes with TrpO- subtle differences are found. These differences, which disappear when excess methanol is used, are ascribed to the presence of weak forces, such as hydrophobic or d-π interactions.
The ternary copper(II) complex of 6-deoxy-6-[(2-(4-imidazolyl)ethyl)amino]cyclomaltoheptaose (CDhm) and L-tryptophanate (L-TrpO-) was characterized by ESR and X-ray diffraction. The solid state structure of [Cu(CDhm)-(L-TrpO)]+ shows that the aromatic side chain of TrpO- is outside the cavity and that the two amino nitrogen atoms, one from the histamine molecule and one from the amino acidate, are in a cis disposition. The two amino nitrogens, the imidazole nitrogen, and the carboxylate oxygen atoms form the base of a square pyramid, which surrounds the copper(II) ion, a water molecule occupying an apical position. Atomic distances suggest for this complex that π-π and d-π interactions could occur in the solid state. Morover, the [Cu(CDhm)(L-TrpO)]+ has a self-assembled structure in which a CDhm molecule behaves as host and as guest. The imidazole and the indole ring are directed into the cavity of an adjacent CDhm molecule from the wider cyclodextrin rim, thus forming a polymeric column structure. ESR spectra were run on the copper(II) ternary complexes with L- or D-tryptophanate and L- or D-alaninate in frozen aqueous solution and on the former pair of enantiomers in the solid state, as well. While in the case of the ternary complex with L- or D-alaninate no differences are observed in their frozen solution spectra, in the case of complexes with TrpO- subtle differences are found. These differences, which disappear when excess methanol is used, are ascribed to the presence of weak forces, such as hydrophobic or d-π interactions.
Crystal and Molecular Structure of the [6-Deoxy-6-[(2-(4-imidazolyl)ethyl)amino]cyclomaltoheptaose]copper(II) Ternary Complex with L-Tryptophanate. Role of Weak Forces in the Chiral Recognition Process Assisted by a Metallocyclodextrin
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Crystal and Molecular Structure of the [6-Deoxy-6-[(2-(4-imidazolyl)ethyl)amino]cyclomaltoheptaose]copper(II) Ternary Complex with L-Tryptophanate. Role of Weak Forces in the Chiral Recognition Process Assisted by a Metallocyclodextrin
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Impact Factor: 2.15
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Di Blasio B, Galdiero S, Saviano M, Pedone C, Benedetti E, Rizzarelli E, Pedotti S, Vecchio G, Gibbons WA
Synthesis And Structural Characterization Of 6i, 6ii-Diamino-6i, 6ii-Dideoxy-Cyclomaltoheptaose, A Difunctionalized Beta-Cyclodextrin (426 views)
Carbohydr Res, 1996 Feb 28; 282(1): 41-52.
Impact Factor: 0
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Cucinotta V, Grasso G, Pedotti S, Rizzarelli E, Vecchio G, Di Blasio B, Isernia C, Saviano M, Pedone C
A Platinum(II) Diamino-β-cyclodextrin Complex: A Crystallographic and Solution Study. Synthesis and Structural Characterization of a Platinum(II) Complex of 6A, 6B-Diamino-6A, 6B-dideoxycyclomaltoheptaose (410 views)
Inorg Chem (ISSN: 0020-1669, 1520-510x, 1520-510xelectronic), 1996; 35(26): 7535-7540.
Impact Factor: 2.736
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Di Blasio B, Galdiero S, Saviano M, De Simone G, Benedetti E, Pedone C, Gibbons WA, Deschenaux R, Rizzarelli E, Vecchio G
Functionalized cyclodextrins: Synthesis and structural characterization of 6-deoxy-6-{4-[N-tert-butoxycarbonyl-2-aminoethyl]-imidazolyl}-cyclomaltoheptaose (326 views)
Supramol Chem (ISSN: 1061-0278), 1996; 7(1): 47-54.
Impact Factor: 3.19
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Alberghina M, Brogna A, Mangiameli A, Marletta F, Rizzarelli E, Sammartano S
Copper(II) complexes of aminoacids: Gastric acid antisecretory activity in rats (2114 views)
Farmaco Ed Sci, 1982 Dec; 37(12): 805-814.
Impact Factor: 0
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9 Records (8 excluding Abstracts).
Total impact factor: 18.45 (16.3 excluding Abstracts).
Total 5 year impact factor: 20.443 (17.442 excluding Abstracts).
Total impact factor: 18.45 (16.3 excluding Abstracts).
Total 5 year impact factor: 20.443 (17.442 excluding Abstracts).
314 views. Last view on Saturday 14 January 2023, 20:29:50
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