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Hydrogen Bonded Supramolecular Assembly in N 6-Benzyladeninium Nitrate and N 6-Benzyladeninium 3-Hydroxy Picolinate: A Synthetic Cytokinin

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Abstract

N6-benzyladeninium nitrate, (1), C12H12N5+ NO3− crystallizes in P21/c, with a = 15.0035(13), b = 5.3788(5), c = 16.8954(13) Å, β = 107.331(6)°, Z = 4 and N6-benzyladeninium 3-hydroxy picolinate, (2), C12H12N5+ C6H4NO3−, crystallizes in P1, with a = 8.3017(4), b = 14.6170(7), c = 14.7909 (8) Å, α = 78.801 (4), β = 81.979 (4),γ = 88.849 (4)°, Z = 4. In both the salts, the cation exists as N(7)H tautomer with protonation at the N3 atom. The dihedral angle of 76.64 (16)° for (1), 67.91(12)° for (cation A) and 68.27 (13)° for (cation B) in (2), between the adenine plane and phenyl ring plane, the distal orientation of the N6 substituent with respect to the imidazole ring and the free N1 position, make these benzyladeninium cations meet all the requirements necessary for cytokinin activity. The crystal structures are stabilized by N–H···N, N–H···O, C–H···O hydrogen bonds and C–H···π stacking interaction between symmetry related benzyladenine molecule.

Graphical Abstract

Supramolecular architectures in the crystal structures of N 6-Benzyladeninium nitrate and N 6-Benzyladeninium 3-hydroxy picolinate salts.

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Acknowledgments

JSN thanks the UGC-SAP, India, for the award of RFSMS. The authors thank the D.S.T-India (F·I.S.T programme) for the use of Bruker SMART APEX II diffractometer at the School of Chemistry, Bharathidasan University, Tiruchirappalli, Tamilnadu, India.

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  1. School of Chemistry, Bharathidasan University, Tiruchirappalli, 620 024, Tamilnadu, India

    Jeyaraman Selvaraj Nirmalram, Duraisamy Tamilselvi & Packianathan Thomas Muthiah

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  1. Jeyaraman Selvaraj Nirmalram
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  2. Duraisamy Tamilselvi
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  3. Packianathan Thomas Muthiah
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Correspondence to Packianathan Thomas Muthiah.

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Nirmalram, J.S., Tamilselvi, D. & Muthiah, P.T. Hydrogen Bonded Supramolecular Assembly in N 6-Benzyladeninium Nitrate and N 6-Benzyladeninium 3-Hydroxy Picolinate: A Synthetic Cytokinin. J Chem Crystallogr 41, 864–867 (2011). https://doi.org/10.1007/s10870-011-0014-x

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