Wiley, Journal of Physical Organic Chemistry, 8(10), p. 637-645, 1997
DOI: 10.1002/(sici)1099-1395(199708)10:8<637::aid-poc930>3.0.co;2-p
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The molecular and crystal structure of 3-nitropyrazole was determined by X-ray analysis. The triclinic unit cell contains 12 molecules which form four hydrogen-bonded (N—H···N) trimers. Each trimer comprises of pseudo-ring in a flattened envelope distorted towards a chair conformation. The crystal packing consists of layers formed by centrosymmetric related trimers joined through C—H···O interactions. Ab initio calculations were performed on 3(5)-nitro- and 4-nitropyrazole and their corresponding protonated forms up to the MP2/6–31G** level of theory. The origin of the difference in aqueous basicities between both nitropyrazoles is discussed. © 1997 John Wiley & Sons, Ltd.