Tuning dihydrogen bonds: Enhanced solid-state reactivity in a dihydrogen-bonded system with exceptionally short H ··· H distances

Angewandte Chemie - International Edition

Volumn 38, Issue 11, 1999, Pages 1661-1663

  Custelcean, Radu ^a   Jackson, James E ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

Hydrides; Hydrogen bonds; Solid state chemistry; Topochemistry

Indexed keywords

TRIETHANOLAMINE;

ACIDITY; ALKALINITY; ARTICLE; COVALENT BOND; CRYSTAL STRUCTURE; DECOMPOSITION; DIMERIZATION; HYDROGEN BOND; MELTING POINT; MOLECULAR INTERACTION; SOLID STATE; X RAY POWDER DIFFRACTION;

EID: 0033152143     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990601)38:11<1661::AID-ANIE1661>3.0.CO;2-O     Document Type: Article

References (14)

1. See for example: a) R. H. Crabtree, P. E. M. Siegbahn, O. Eisenstein, A. L. Rheingold, T. F. Koetzle, Acc. Chem. Res. 1996, 29, 348-354;
2. b) A. J. Lough, S. Park, R. Ramachandran, R. H. Morris, J. Am. Chem. Soc. 1994, 116, 8356-8357;
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4. d) J. P. Campbell, J. W. Hwang, V. G. Young, R. B Von Dreele, C. J. Cramer, W. L. Gladfelter, J. Am. Chem. Soc. 1998, 120, 521-531;
5. e) I. Alkorta, I. Rozas, J. Elguero, Chem. Soc. Rev. 1998, 27, 163-170;
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7. R. Custelcean, J. E. Jackson, J. Am. Chem. Soc. 1998, 120, 12935-12941.
8. 7Li solid-state MAS NMR: δ = 2.8 (1.5).
9. -3. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-105289. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ. UK (fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
10. The typical normalization of O-H and B-H bonds to 0.96 and 1.21 Å, respectively, leads to the more realistic H-H distances of 1.62-2.28 Å.
11. 2O) yielded distances 0.04 Å longer on average than the final neutron diffraction values.
12. We found the 1.73 Å as the shortest reliable H-H contact distance for a dihydrogen bond reported so far (ref. [1a]). Another value of 1.68 Å was reported, but the disorder of the proton donor solvent as well as the uncertainty in its N-H proton location make this distance somewhat less reliable. See: B. P. Patel, W. Yao, G. P. A. Yap, A. L. Rheingold, R. H. Crabtree, Chem. Commun. 1996, 991-992.
13. Using lower temperatures for decomposition (down to 65°C) did not improve the crystallinity of this material.
14. R. E. Davis, J. A. Gottbrath, J. Am. Chem. Soc. 1962, 84, 895-898.