Kumara Swamy, K. C. ; Kumaraswamy, Sudha ; Kommana, Praveen (2001) Very strong C-H···O, N-H···O, and O-H···O hydrogen bonds involving a cyclic phosphate Journal of the American Chemical Society, 123 (50). pp. 12642-12649. ISSN 0002-7863
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Official URL: http://pubs.acs.org/doi/abs/10.1021/ja010713x
Related URL: http://dx.doi.org/10.1021/ja010713x
Abstract
Very short C-H···O, N-H··O, and O-H···O hydrogen bonds have been generated utilizing the cyclic phosphate [CH2(6-t-Bu-4-Me-C6H2O)2]P(O)OH (1). X-ray structures of (i) 1 (unsolvated, two polymorphs), 1.EtOH, and 1.MeOH, (ii) [imidazolium]+[CH2(6-t-Bu-4-Me-C6H2O)2PO2 ]-.MeOH [2], (iii) [HNC5H4-N=N-C5H4NH]2+[{CH2(6-t-Bu-4 -Me-C6H2O)2PO2}2]2-.4CH3 CN.H2O [3], (v) [K, 18-crown-6]+[{CH2(6-t-Bu-4-Me-C6H2O)2P(O)OH}{C H2(6-t-Bu-4-Me-C6H2O)2PO2}]-.2THF [4], (vi) 1.cytosine.MeOH [5], (vii) 1.adenine.½MeOH [6], and (viii) 1.S-(-)-proline [7] have been determined. The phosphate 1 in both its forms is a hydrogen-bonded dimer with a short O-H···O distance of 2.481(2) [triclinic form] or 2.507(3) Å[monoclinic form]. Compound 2 has a helical structure with a very short C-H···O hydrogen bond involving an imidazolyl C-H and methanol in addition to N-H···O hydrogen bonds. A helical motif is also seen in 5. In 3, an extremely short NH···O hydrogen bond [N···O 2.558(4) Å ] is observed. Compounds 6 and 7 also exhibit short NH···O hydrogen bonds. In 1.EtOH, a 12-membered hydrogen-bonded ring motif, with one of the shortest known OH···O hydrogen bonds [O···O 2.368(4) Å ], is present. 1.MeOH is a similar dimer with a very short O(H)···O bond [2.429(3) Å ]. In 4, the deprotonated phosphate (anion) and the parent acid are held together by a hydrogen bond on one side and a coordinate/covalent bond to potassium on the other; the O-H···O bond is symmetrical and very strong [O· · ·O 2.397(3) Å].
Item Type: | Article |
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Source: | Copyright of this article belongs to American Chemical Society. |
ID Code: | 29604 |
Deposited On: | 20 Dec 2010 07:58 |
Last Modified: | 07 Jun 2011 05:59 |
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