2-Amino-6-methylpyridine based co-crystal salt formation using succinic acid

 The current work reports the formation methodology of the co-crystal between 2-amino-6-methylpyridine and succinic acid, its single-crystal characterization, and the computational study. The single-crystal analysis showed that the co-crystal molecules are interlinked by N···H−O and O···H−O bonds to form the R22 (8) loop and D22 (5) and D22 (8) finite pattern along with the formation of the infinite 2D network in the (1 0 1 bar) plane having base vectors [1 0 1] and [0 1 bar 0]. Moreover, the weak interactions of the π-π stacking type and Csbnd O-Cg interactions are found in the title compound helping further strengthen the crystal structure. 

The Hirshfeld surface analysis confirmed that H···H interatomic contacts are the most significant contributor to entire interatomic contacts with a contribution of 45.8%. 

The computational studies supported the presence of significantly strong hydrogen bonds within the title complex. The molecular orbital analysis suggested that both HOMO/HOMO-1 and LUMO/LUMO+1 could participate in the complex's oxidative-reductive processes.

The HOMO has dominating contributions from one succinate unit and minor contributions from the H-bonded NH2-group of the neighboring 2-amino-6-methyl pyridine-1-ium moiety. The calculated values of the global reactivity parameters suggest noticeable stability of the title complex. It was also shown to possess quite pronounced nonlinear optical properties.

Highlights

•Effective production of the novel 2-amino-6-methylpyridine co-crystal salt.

•Salt stabilization by ionic interactions, hydrogen bonds, and stacking interactions.

•DFT study supports the existence of quite strong intracomplex hydrogen bonding.

•Current compounds can have potential future applications in pharmacology.

Formula: C6H8N2

Molecular weight: 108.1411

IUPAC Standard InChI: InChI=1S/C6H8N2/c1-5-3-2-4-6(7)8-5/h2-4H,1H3,(H2,7,8) Copy

InChI version 1.06

IUPAC Standard InChIKey: QUXLCYFNVNNRBE-UHFFFAOYSA-N Copy

CAS Registry Number: 1824-81-3

Chemical structure: C6H8N2

This structure is also available as a 2d Mol file or as a computed 3d SD file

The 3d structure may be viewed using Java or Javascript.

Other names: 2-Picoline, 6-amino-; 2-Amino-6-methylpyridine; 2-Amino-6-picoline; 6-Amino-2-methylpyridine; 6-Amino-2-picoline; 6-Methyl-2-pyridinamine; 6-Methyl-2-pyridylamine; Pyridine, 2-amino-6-methyl-; 6-Methyl-2-aminopyridine; NSC 1488; NSC 6971