Biguanide

Ernst, S. R.; Cagle, F. W.

doi:10.1107/s0567740877003197

Cited by 31 publications

(20 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[Cambridge Structural Database (Allen, 2002) refcodes HDCADPZ (Privett et al, 1987); BIGUAN (Pinkerton & Schwarzenbach, 1978) and BIGUAN01 (Ernst & Cagle, 1977); NIWCAY (Zheng et al, 2007)]. The molecular structure of the new compounds (I)-(V) is reminiscent of diiminoisoindoline (Zhang, Njus et al, 2004), including the observation of the amino tautomer in the solid state.…”

Section: Figurementioning

confidence: 99%

See 1 more Smart Citation

Five relatedN′-(2,2,2-trichloroethanimidoyl)benzene-1-carboximidamides

et al. 2011

View full text Add to dashboard Cite

In the solid state, 4-methoxy-N'-(2,2,2-trichloroethanimidoyl)benzene-1-carboximidamide, C(10)H(10)Cl(3)N(3)O, (I), N'-(2,2,2-trichloroethanimidoyl)benzene-1-carboximidamide, C(9)H(8)Cl(3)N(3), (II), 4-chloro-N'-(2,2,2-trichloroethanimidoyl)benzene-1-carboximidamide, C(9)H(7)Cl(4)N(3), (III), 4-bromo-N'-(2,2,2-trichloroethanimidoyl)benzene-1-carboximidamide, C(9)H(7)BrCl(3)N(3), (IV), and 4-trifluoromethyl-N'-(2,2,2-trichloroethanimidoyl)benzene-1-carboximidamide, C(10)H(7)Cl(3)F(3)N(3), (V), display strong intramolecular N-H...N hydrogen bonding across the chelate ring and also intramolecular N-H...Cl contacts. Additional intermolecular hydrogen bonds link the molecules into chains, double chains or sheets in all cases except for compound (V). For compound (II), there are three independent molecules per asymmetric unit.

show abstract

Section: Figurementioning

confidence: 99%

“…Hydrogen-bond geometry (Å , ) for (V). Average bond lengths (Å ) and angles ( ) for compounds (I)-(V), and comparison with the averages in two biguanides [CSD refcodes BIGUAN01 (Ernst & Cagle, 1977) and NIWCAY (Zheng et al, 2007)]. Average in biguanides N1-C1 1.327 (5) 1.325 (2) N1-C1-N2 125.6 (2) 128.6 (2) C1-N2…”

Section: Tablementioning

confidence: 99%

Five relatedN′-(2,2,2-trichloroethanimidoyl)benzene-1-carboximidamides

et al. 2011

View full text Add to dashboard Cite

show abstract

“…Few structures of simple biguanidinium salts or biguanides have been reported (25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37)(38), and in none of these cases have aryl groups been present at positions 1 and 5. As a result, we elected to determine the structures of 1,5-diphenylbiguanide (6a) and its monohydrochloride salt.…”

Section: Crystal Structures Of 15-diphenylbiguanide (6a) and Its Monmentioning

confidence: 99%

A practical guide to arylbiguanides Synthesis and structural characterization

Lebel¹,

Maris²,

Duval³

et al. 2005

Can. J. Chem.

View full text Add to dashboard Cite

Monohydrochloride salts of diverse 1-arylbiguanides and 1,5-diarylbiguanides were synthesized by the reaction of anilinium chlorides with dicyandiamide or sodium dicyanamide, and the biguanidinium chlorides were converted into the corresponding biguanides by deprotonation with methanolic NaOCH3. The resulting biguanides and their salts were fully characterized by spectroscopic methods, and the structures of representative compounds were determined by X-ray crystallography.Key words: biguanide, biguanidinium, synthesis, structure, hydrogen bonds, noncovalent interactions, supramolecular chemistry.

show abstract

“…Even with the availability of this H atom not otherwise involved in coordination, N(00) does not enter into the hydrogen-bonding scheme. This is somewhat unexpected since the crystal structure of unprotonated biguanide (Ernst & Cagle, 1977) Table 1 are represented by the symmetry operation (55501).…”

mentioning

confidence: 99%