Association of dicyanodiphenylacetylenes with silver(I) salts in solution and solid state: Electrospray ionization mass spectrometry samples aggregates at subsaturated concentrations

Journal of the American Chemical Society

Volumn 119, Issue 43, 1997, Pages 10401-10412

  Hirsch, Keith A ^a   Wilson, Scott R ^a   Moore, Jeffrey S ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; SILVER DERIVATIVE;

ARTICLE; CRYSTALLIZATION; CRYSTALLOGRAPHY; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; MOLECULAR MODEL; REACTION ANALYSIS;

EID: 0030660172     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971135g     Document Type: Article

References (39)

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9. For studies of noncovalent aggregation by electrospray ionization mass spectrometry, see: (a) Cheng, X.; Gao, Q.; Smith, R. D.; Simanek, E. E.; Mammen, M.; Whitesides, G. M. J. Org. Chem. 1996, 61, 2204-2206. (b) Fujita, M.; Ibukuro, F.; Hagihara, H.; Ogura, K. Nature 1994, 367, 720-723. (c) Manna, J.; Whiteford, J. A.; Stang, P. J.; Muddiman, D. C; Smith, R. D. J. Am. Chem. Soc. 1996, 118, 8731-8732. (d) Langley, G. J.; Hecquet, E.; Morris, I. P.; Hamilton, D. G. Rapid Commun. Mass Spectrom. 1997, 11, 165-170. (e) Marquis-Rigault, A.; Dupont-Gervais, A.; Van Dorsselaer, A.; Lehn, J.-M. Chem. Eur. J. 1996, 2, 1395-1398. (f) Funeriu, D. P.; Lehn, J.-M.; Baum, G.; Fenske, D. Chem. Eur. J. 1997, 3, 99-104. (g) Moucheron, C.; Kirsch-De Mesmaeker, A.; Dupont-Gervais, A.; Leize, E.; Van Dorsselaer, A. J. Am. Chem. Soc. 1996, 118, 12834-12835. (h) Przybylski, M.; Glocker, M. O. Angew. Chem., Int. Ed. Engl. 1996, 35, 806-826.
10. For studies of noncovalent aggregation by electrospray ionization mass spectrometry, see: (a) Cheng, X.; Gao, Q.; Smith, R. D.; Simanek, E. E.; Mammen, M.; Whitesides, G. M. J. Org. Chem. 1996, 61, 2204-2206. (b) Fujita, M.; Ibukuro, F.; Hagihara, H.; Ogura, K. Nature 1994, 367, 720-723. (c) Manna, J.; Whiteford, J. A.; Stang, P. J.; Muddiman, D. C; Smith, R. D. J. Am. Chem. Soc. 1996, 118, 8731-8732. (d) Langley, G. J.; Hecquet, E.; Morris, I. P.; Hamilton, D. G. Rapid Commun. Mass Spectrom. 1997, 11, 165-170. (e) Marquis-Rigault, A.; Dupont-Gervais, A.; Van Dorsselaer, A.; Lehn, J.-M. Chem. Eur. J. 1996, 2, 1395-1398. (f) Funeriu, D. P.; Lehn, J.-M.; Baum, G.; Fenske, D. Chem. Eur. J. 1997, 3, 99-104. (g) Moucheron, C.; Kirsch-De Mesmaeker, A.; Dupont-Gervais, A.; Leize, E.; Van Dorsselaer, A. J. Am. Chem. Soc. 1996, 118, 12834-12835. (h) Przybylski, M.; Glocker, M. O. Angew. Chem., Int. Ed. Engl. 1996, 35, 806-826.
11. For studies of noncovalent aggregation by electrospray ionization mass spectrometry, see: (a) Cheng, X.; Gao, Q.; Smith, R. D.; Simanek, E. E.; Mammen, M.; Whitesides, G. M. J. Org. Chem. 1996, 61, 2204-2206. (b) Fujita, M.; Ibukuro, F.; Hagihara, H.; Ogura, K. Nature 1994, 367, 720-723. (c) Manna, J.; Whiteford, J. A.; Stang, P. J.; Muddiman, D. C; Smith, R. D. J. Am. Chem. Soc. 1996, 118, 8731-8732. (d) Langley, G. J.; Hecquet, E.; Morris, I. P.; Hamilton, D. G. Rapid Commun. Mass Spectrom. 1997, 11, 165-170. (e) Marquis-Rigault, A.; Dupont-Gervais, A.; Van Dorsselaer, A.; Lehn, J.-M. Chem. Eur. J. 1996, 2, 1395-1398. (f) Funeriu, D. P.; Lehn, J.-M.; Baum, G.; Fenske, D. Chem. Eur. J. 1997, 3, 99-104. (g) Moucheron, C.; Kirsch-De Mesmaeker, A.; Dupont-Gervais, A.; Leize, E.; Van Dorsselaer, A. J. Am. Chem. Soc. 1996, 118, 12834-12835. (h) Przybylski, M.; Glocker, M. O. Angew. Chem., Int. Ed. Engl. 1996, 35, 806-826.
12. For studies of noncovalent aggregation by electrospray ionization mass spectrometry, see: (a) Cheng, X.; Gao, Q.; Smith, R. D.; Simanek, E. E.; Mammen, M.; Whitesides, G. M. J. Org. Chem. 1996, 61, 2204-2206. (b) Fujita, M.; Ibukuro, F.; Hagihara, H.; Ogura, K. Nature 1994, 367, 720-723. (c) Manna, J.; Whiteford, J. A.; Stang, P. J.; Muddiman, D. C; Smith, R. D. J. Am. Chem. Soc. 1996, 118, 8731-8732. (d) Langley, G. J.; Hecquet, E.; Morris, I. P.; Hamilton, D. G. Rapid Commun. Mass Spectrom. 1997, 11, 165-170. (e) Marquis-Rigault, A.; Dupont-Gervais, A.; Van Dorsselaer, A.; Lehn, J.-M. Chem. Eur. J. 1996, 2, 1395-1398. (f) Funeriu, D. P.; Lehn, J.-M.; Baum, G.; Fenske, D. Chem. Eur. J. 1997, 3, 99-104. (g) Moucheron, C.; Kirsch-De Mesmaeker, A.; Dupont-Gervais, A.; Leize, E.; Van Dorsselaer, A. J. Am. Chem. Soc. 1996, 118, 12834-12835. (h) Przybylski, M.; Glocker, M. O. Angew. Chem., Int. Ed. Engl. 1996, 35, 806-826.
13. For studies of noncovalent aggregation by electrospray ionization mass spectrometry, see: (a) Cheng, X.; Gao, Q.; Smith, R. D.; Simanek, E. E.; Mammen, M.; Whitesides, G. M. J. Org. Chem. 1996, 61, 2204-2206. (b) Fujita, M.; Ibukuro, F.; Hagihara, H.; Ogura, K. Nature 1994, 367, 720-723. (c) Manna, J.; Whiteford, J. A.; Stang, P. J.; Muddiman, D. C; Smith, R. D. J. Am. Chem. Soc. 1996, 118, 8731-8732. (d) Langley, G. J.; Hecquet, E.; Morris, I. P.; Hamilton, D. G. Rapid Commun. Mass Spectrom. 1997, 11, 165-170. (e) Marquis-Rigault, A.; Dupont-Gervais, A.; Van Dorsselaer, A.; Lehn, J.-M. Chem. Eur. J. 1996, 2, 1395-1398. (f) Funeriu, D. P.; Lehn, J.-M.; Baum, G.; Fenske, D. Chem. Eur. J. 1997, 3, 99-104. (g) Moucheron, C.; Kirsch-De Mesmaeker, A.; Dupont-Gervais, A.; Leize, E.; Van Dorsselaer, A. J. Am. Chem. Soc. 1996, 118, 12834-12835. (h) Przybylski, M.; Glocker, M. O. Angew. Chem., Int. Ed. Engl. 1996, 35, 806-826.
14. For studies of noncovalent aggregation by electrospray ionization mass spectrometry, see: (a) Cheng, X.; Gao, Q.; Smith, R. D.; Simanek, E. E.; Mammen, M.; Whitesides, G. M. J. Org. Chem. 1996, 61, 2204-2206. (b) Fujita, M.; Ibukuro, F.; Hagihara, H.; Ogura, K. Nature 1994, 367, 720-723. (c) Manna, J.; Whiteford, J. A.; Stang, P. J.; Muddiman, D. C; Smith, R. D. J. Am. Chem. Soc. 1996, 118, 8731-8732. (d) Langley, G. J.; Hecquet, E.; Morris, I. P.; Hamilton, D. G. Rapid Commun. Mass Spectrom. 1997, 11, 165-170. (e) Marquis-Rigault, A.; Dupont-Gervais, A.; Van Dorsselaer, A.; Lehn, J.-M. Chem. Eur. J. 1996, 2, 1395-1398. (f) Funeriu, D. P.; Lehn, J.-M.; Baum, G.; Fenske, D. Chem. Eur. J. 1997, 3, 99-104. (g) Moucheron, C.; Kirsch-De Mesmaeker, A.; Dupont-Gervais, A.; Leize, E.; Van Dorsselaer, A. J. Am. Chem. Soc. 1996, 118, 12834-12835. (h) Przybylski, M.; Glocker, M. O. Angew. Chem., Int. Ed. Engl. 1996, 35, 806-826.
15. For examples of coordination networks prepared with 4,4′-bipyridine, see: (a) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Chem. Soc., Chem. Commun. 1994, 2755-2756. (b) MacGillivray, L. R.; Subramanian, S.; Zaworotko, M. J. J. Chem. Soc., Chem. Commun. 1994, 1325-1326. (c) Robinson, F.; Zaworotko, M. J. J. Chem. Soc., Chem. Commun. 1995, 2413-2414. (d) Losier, P.; Zaworotko, M. J. Angew Chem., Int. Ed. Engl. 1996, 35, 2779-2782. (e) Yaghi, O. M.; Li, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 207-209. (f) Yaghi, O. M.; Li, H. J. Am. Chem. Soc. 1995, 117, 10401-10402. (g) Yaghi, O. M.; Li, H. J. Am. Chem. Soc. 1996, 118, 295-296.
16. For examples of coordination networks prepared with 4,4′-bipyridine, see: (a) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Chem. Soc., Chem. Commun. 1994, 2755-2756. (b) MacGillivray, L. R.; Subramanian, S.; Zaworotko, M. J. J. Chem. Soc., Chem. Commun. 1994, 1325-1326. (c) Robinson, F.; Zaworotko, M. J. J. Chem. Soc., Chem. Commun. 1995, 2413-2414. (d) Losier, P.; Zaworotko, M. J. Angew Chem., Int. Ed. Engl. 1996, 35, 2779-2782. (e) Yaghi, O. M.; Li, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 207-209. (f) Yaghi, O. M.; Li, H. J. Am. Chem. Soc. 1995, 117, 10401-10402. (g) Yaghi, O. M.; Li, H. J. Am. Chem. Soc. 1996, 118, 295-296.
17. For examples of coordination networks prepared with 4,4′-bipyridine, see: (a) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Chem. Soc., Chem. Commun. 1994, 2755-2756. (b) MacGillivray, L. R.; Subramanian, S.; Zaworotko, M. J. J. Chem. Soc., Chem. Commun. 1994, 1325-1326. (c) Robinson, F.; Zaworotko, M. J. J. Chem. Soc., Chem. Commun. 1995, 2413-2414. (d) Losier, P.; Zaworotko, M. J. Angew Chem., Int. Ed. Engl. 1996, 35, 2779-2782. (e) Yaghi, O. M.; Li, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 207-209. (f) Yaghi, O. M.; Li, H. J. Am. Chem. Soc. 1995, 117, 10401-10402. (g) Yaghi, O. M.; Li, H. J. Am. Chem. Soc. 1996, 118, 295-296.
18. For examples of coordination networks prepared with 4,4′-bipyridine, see: (a) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Chem. Soc., Chem. Commun. 1994, 2755-2756. (b) MacGillivray, L. R.; Subramanian, S.; Zaworotko, M. J. J. Chem. Soc., Chem. Commun. 1994, 1325-1326. (c) Robinson, F.; Zaworotko, M. J. J. Chem. Soc., Chem. Commun. 1995, 2413-2414. (d) Losier, P.; Zaworotko, M. J. Angew Chem., Int. Ed. Engl. 1996, 35, 2779-2782. (e) Yaghi, O. M.; Li, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 207-209. (f) Yaghi, O. M.; Li, H. J. Am. Chem. Soc. 1995, 117, 10401-10402. (g) Yaghi, O. M.; Li, H. J. Am. Chem. Soc. 1996, 118, 295-296.
19. For examples of coordination networks prepared with 4,4′-bipyridine, see: (a) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Chem. Soc., Chem. Commun. 1994, 2755-2756. (b) MacGillivray, L. R.; Subramanian, S.; Zaworotko, M. J. J. Chem. Soc., Chem. Commun. 1994, 1325-1326. (c) Robinson, F.; Zaworotko, M. J. J. Chem. Soc., Chem. Commun. 1995, 2413-2414. (d) Losier, P.; Zaworotko, M. J. Angew Chem., Int. Ed. Engl. 1996, 35, 2779-2782. (e) Yaghi, O. M.; Li, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 207-209. (f) Yaghi, O. M.; Li, H. J. Am. Chem. Soc. 1995, 117, 10401-10402. (g) Yaghi, O. M.; Li, H. J. Am. Chem. Soc. 1996, 118, 295-296.
20. For examples of coordination networks prepared with 4,4′-bipyridine, see: (a) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Chem. Soc., Chem. Commun. 1994, 2755-2756. (b) MacGillivray, L. R.; Subramanian, S.; Zaworotko, M. J. J. Chem. Soc., Chem. Commun. 1994, 1325-1326. (c) Robinson, F.; Zaworotko, M. J. J. Chem. Soc., Chem. Commun. 1995, 2413-2414. (d) Losier, P.; Zaworotko, M. J. Angew Chem., Int. Ed. Engl. 1996, 35, 2779-2782. (e) Yaghi, O. M.; Li, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 207-209. (f) Yaghi, O. M.; Li, H. J. Am. Chem. Soc. 1995, 117, 10401-10402. (g) Yaghi, O. M.; Li, H. J. Am. Chem. Soc. 1996, 118, 295-296.
21. For examples of coordination networks prepared with 4,4′-bipyridine, see: (a) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Chem. Soc., Chem. Commun. 1994, 2755-2756. (b) MacGillivray, L. R.; Subramanian, S.; Zaworotko, M. J. J. Chem. Soc., Chem. Commun. 1994, 1325-1326. (c) Robinson, F.; Zaworotko, M. J. J. Chem. Soc., Chem. Commun. 1995, 2413-2414. (d) Losier, P.; Zaworotko, M. J. Angew Chem., Int. Ed. Engl. 1996, 35, 2779-2782. (e) Yaghi, O. M.; Li, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 207-209. (f) Yaghi, O. M.; Li, H. J. Am. Chem. Soc. 1995, 117, 10401-10402. (g) Yaghi, O. M.; Li, H. J. Am. Chem. Soc. 1996, 118, 295-296.
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