2-Methyl-4-(4-pyridyl)-3-butyn-2-ol: a two-dimensional hydrogen-bond network

Pollagi, Timothy P.; Geib, Steven J.; Hopkins, Michael D.

doi:10.1107/s0108270193010455

Cited by 1 publication

(2 citation statements)

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“…This suggests that the polarized form (IIa) is only a minor contributor to the overall electronic structure. The triple bond lengths in (I) and (II) range from 1.193 (2) to 1.196 (4) Å and are in agreement with the values reported for similar structures (Singelenberg & van Eijck, 1987;Pollagi et al, 1994;Aakerö y et al, 2005Aakerö y et al, , 2007Aakerö y et al, , 2009.…”

Section: Figuresupporting

confidence: 88%

“…Similarly to (I), both OH groups are twisted to the same side of the approximate plane defined by the amino group and pyrimidine ring, with O1-C7-C2-N1 and O2-C12-C4-N2 torsion angles of À57.66 (16) and 24.00 14, respectively. Remarkably, the two triple bonds deviate from the approximate plane, with C2-C5-C6 and C4-C10-C11 angles of 169.57 (16) and 171.94 17, respectively, which are smaller than those in (I) and in similar structures (Singelenberg & van Eijck, 1987;Pollagi et al, 1994;Aakerö y et al, 2005Aakerö y et al, , 2007Aakerö y et al, , 2009. This bend meets the stereochemical demand for dimer formation in the supramolecular structure.…”

Section: Commentmentioning

confidence: 77%

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Supramolecular structures constructed by 3-(2-amino-6-chloropyrimidin-4-yl)-1,1-dimethylprop-2-yn-1-ol monohydrate and 3-[2-amino-6-(3-hydroxy-3,3-dimethylprop-1-yn-1-yl)pyrimidin-4-yl]-1,1-dimethylprop-2-yn-1-ol

et al. 2011

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The molecule of 3-(2-amino-6-chloropyrimidin-4-yl)-1,1-dimethylprop-2-yn-1-ol monohydrate, C(9)H(10)ClN(3)O·H(2)O, (I), shows a very polarized molecular-electronic structure, while the polarization is slight for 3-[2-amino-6-(3-hydroxy-3,3-dimethylprop-1-yn-1-yl)pyrimidin-4-yl]-1,1-dimethylprop-2-yn-1-ol, C(14)H(17)N(3)O(2), (II). In the supramolecular structure of (I), a combination of hard N-H···N hydrogen bonds and soft C-H···N hydrogen bonds creates a molecular column. Aromatic π-π stackings between the pyrimidine rings stabilize the column with perpendicular and centroid-centroid distances of 3.283 (3) and 3.588 (1) Å, respectively. Short Cl···Cl contacts further link neighbouring molecular columns, creating a hydrophilic tube in which water molecules are fixed by various hydrogen bonds. In the packing of (II), a one-dimensional molecular chain is formed through several contacts involving hard N-H···O(N) and O-H···O(N) and soft C-H···O hydrogen bonds. Interchain O-H···O hydrogen bonds link the chains giving a two-dimensional stepped network. It is anticipated that study of the influence of hydrogen bonding on the patterns of base pairing and molecular packing in aminopyrimidine structures will shed significant light on nucleic acid structures as well as their functions.

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