The solid-state supramolecular structure of 6-methylisocytosine dihydrogen monophosphate adduct [2-NH(2)-6-CH(3)-C(4)H(2)N(2)O(2)](2)(+) center dot H(2)PO(4)(-), has been determined by single-crystal X-ray diffraction at room temperature. In this paper a revised model, based on single proton transfer from one molecule of phosphoric acid to the pyridine N atoms opposite to the methyl substituent of the two aminooxo tautomers of 6-methylisocytosine, has been used for the crystal structure analysis of the ionic complex. 6-Methylisocytosine molecules form hemiprotonated centrosymmetric pairs by complementary WC triple hydrogen bonds. Dihydrogen phosphate anions act as bridges between charged WC dimers to generate ribbons via four cation-to-anion N-H center dot center dot center dot O hydrogen bonds. Ribbons are then interconnected to form a three-dimensional network by means of a further series of O-H center dot center dot center dot O anion-to-cation hydrogen bonds. (C) 2011 Elsevier B.V. All rights reserved.

Supramolecular structure of unnatural nucleobases: Revised structure of (2:1) 6-methylisocytosinium dihydrogen monophosphate adduct / Portalone, Gustavo; Irrera, Simona. - In: JOURNAL OF MOLECULAR STRUCTURE. - ISSN 0022-2860. - STAMPA. - 991:1-3(2011), pp. 92-96. [10.1016/j.molstruc.2011.02.008]

Supramolecular structure of unnatural nucleobases: Revised structure of (2:1) 6-methylisocytosinium dihydrogen monophosphate adduct

PORTALONE, Gustavo;IRRERA, SIMONA
2011

Abstract

The solid-state supramolecular structure of 6-methylisocytosine dihydrogen monophosphate adduct [2-NH(2)-6-CH(3)-C(4)H(2)N(2)O(2)](2)(+) center dot H(2)PO(4)(-), has been determined by single-crystal X-ray diffraction at room temperature. In this paper a revised model, based on single proton transfer from one molecule of phosphoric acid to the pyridine N atoms opposite to the methyl substituent of the two aminooxo tautomers of 6-methylisocytosine, has been used for the crystal structure analysis of the ionic complex. 6-Methylisocytosine molecules form hemiprotonated centrosymmetric pairs by complementary WC triple hydrogen bonds. Dihydrogen phosphate anions act as bridges between charged WC dimers to generate ribbons via four cation-to-anion N-H center dot center dot center dot O hydrogen bonds. Ribbons are then interconnected to form a three-dimensional network by means of a further series of O-H center dot center dot center dot O anion-to-cation hydrogen bonds. (C) 2011 Elsevier B.V. All rights reserved.
2011
6-methylisocytosine; cocrystal; dihydrogen monophosphate; dna/rna nucleobases; hybrid inorganic-organic compounds; proton-transfer compounds
01 Pubblicazione su rivista::01a Articolo in rivista
Supramolecular structure of unnatural nucleobases: Revised structure of (2:1) 6-methylisocytosinium dihydrogen monophosphate adduct / Portalone, Gustavo; Irrera, Simona. - In: JOURNAL OF MOLECULAR STRUCTURE. - ISSN 0022-2860. - STAMPA. - 991:1-3(2011), pp. 92-96. [10.1016/j.molstruc.2011.02.008]
File allegati a questo prodotto
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/90107
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 19
  • ???jsp.display-item.citation.isi??? 19
social impact