1-(p-Chlorophenyl)biguanide hydrochloride, C8H11ClN5+.Cl−

Brown, Carolyn J.; Sengier, L.

doi:10.1107/s0108270184007691

Cited by 8 publications

(11 citation statements)

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“…3a). The NLN distance in these cationic pairs is 3.033(3) Å. Intercationic hydrogen bonding is inhibited by coulombic repulsion and is absent in most biguanidinium salts (4,11,14,15,17,(19)(20)(21), although it has previously been observed in a few cases (12,13,18). Slightly offset face-to-face aromatic interactions are also observed in the structure of salt 2·2HCl (Fig.…”

Section: Crystal Structure Of the Dihydrochloride Salt Of Bis(biguanimentioning

confidence: 64%

“…It is noteworthy that this uncommon hydrogen-bonded dimeric motif is observed in the structures of both bis(biguanidinium) salts, despite its coulombic disadvantage. Nevertheless, its absence in the structures of most other biguanidinium salts (4,11,14,15,17,(19)(20)(21) suggests that it does not define a motif that can be used reliably in supramolecular construction.…”

Section: Crystal Structure Of the Dihydrochloride Salt Of Bis(biguanimentioning

confidence: 95%

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Hydrogen-bonded networks in crystals built from bis(biguanides) and their salts

Lebel¹,

Maris²,

Wuest³

2006

Can. J. Chem.

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Biguanide groups and biguanidinium cations incorporate multiple sites that can donate or accept hydrogen bonds. To assess their ability to associate and to direct the formation of extended hydrogen-bonded networks, we examined the structure of crystals of four compounds in which two neutral biguanide groups or the corresponding cations are attached to the 1,4-and 1,3-positions of phenylene spacers. As expected, all four structures incorporate extensive networks of hydrogen bonds and reveal other reliable features. In particular, (1) neutral biguanide groups favor a roughly planar conformation with an intramolecular hydrogen bond, and they associate as hydrogen-bonded pairs, (2) despite coulombic repulsion, biguanidinium cations can also associate as hydrogen-bonded pairs, and (3) the 1,3-phenylenebis(biguanidinium) dication favors a pincerlike conformation that allows chelation of suitable counterions. However, the precise patterns of hydrogen bonding in the structures vary substantially, limiting the usefulness of biguanide and biguanidinium as groups for directing supramolecular assembly. Résumé :Des groupes biguanide et des cations biguanidinium incorporent de multiples sites qui peuvent donner ou accepter des liaisons hydrogène. Dans le but d'évaluer la capacité d'associer et de diriger la formation de réseaux étendus de liaisons hydrogène, on a étudié la structure cristalline de quatre composés dans lesquels deux groupes biguanide neutres, ou les cations correspondants, sont attachés aux positions 1,4-et 1,3-de groupes phénylènes. Comme prévu, les quatre structures permettent d'incorporer des réseaux de liaisons hydrogène et mettent en évidence d'autres caracté-ristiques fiables. En particulier, 1) les groupes biguanide neutres favorisent une conformation pratiquement plane avec une liaison hydrogène intramoléculaire et s'associent sous la forme de paires réunies par des liaisons hydrogène, 2) malgré une répulsion coulombique, les cations biguanidinium peuvent aussi former des paires associées par des liaisons hydrogène et 3) le dication phénylène-1,3-bis(biguanidinium) favorise une conformation en forme de pince qui permet d'effectuer une chélation avec des contre-ions appropriés. Toutefois, les régimes précis des liaisons hydrogène varient d'une façon substantielle, ce qui limite l'utilité des groupes biguanide et biguanidinium comme unités pouvant orienter un assemblage supramoléculaire.

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Section: Crystal Structure Of the Dihydrochloride Salt Of Bis(biguanimentioning

confidence: 64%

Section: Crystal Structure Of the Dihydrochloride Salt Of Bis(biguanimentioning

confidence: 95%

Hydrogen-bonded networks in crystals built from bis(biguanides) and their salts

Lebel¹,

Maris²,

Wuest³

2006

Can. J. Chem.

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“…The mean Cl -to N distance is 3.264(4)Å, which is slightly different compared with 3.272(2)Å in the 1-(p-chlorophenyl)biguanide hydrochloride. 6 There is a close resemblance between the dimensions of the biguanide residues in this structure and in 1-(p-chlorophenyl)biguanide hydrochloride.…”

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confidence: 65%

Crystal Structure of 1-(m-Chlorophenyl)biguanide Hydrochloride

López-Olvera¹,

Soriano-Garcı́a²

2004

Anal. Sci. X

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These interactions have also been suggested based on preliminary studies using NG-108-15 cell membranes, which showed that the rate of dissociation of the 5-HT3 receptor antagonist [ 3 H]RS-42358 depends upon the ligand used to prevent rebinding. 2 To characterize further putative allosteric interactions at 5-HT3 receptors, steady-state and kinetic radioligand binding studies have been conducted using the receptor agonist 1-(mchlorophenyl)biguanide. This suggests that the binding of this agonists to unoccupied sites on the receptor can increase the receptor's affinity for prebound ligands, and thereby slow their dissociation. 3,4 In this paper, we describe an X-ray structure determination of 1-(m-chlorophenyl)biguanide hydrochloride. The crystals were prepared from a commercially available compound.X-ray data for crystals of the title compound were collected by graphite-monochromatized Mo Kα radiation at 293 K. No absorption correction was applied. The structure was solved by direct methods and refined by full-matrix least-squares with anisotropic temperature factors for the non-hydrogen atoms. In both molecules, the C4, C5 atoms of the phenyl rings show relatively high temperature factors, which may be due to a localized molecular disorder. The hydrogen atoms bonded to C C8H11Cl2 N5 is monoclinic, P21/n. The unit-cell dimensions at 293 K are a = 9.3569(9), b = 13.6832(14), c = 18.4879(19)Å, β = 98.411(2)˚, V = 2341.6(4)Å 3 , Dx = 1.408 g/cm 3 , and Z = 8. The R value is 0.043 for 4129 reflections. The monoclinic unit cell contains two crystallographic independent molecules, A and B. The Cl(1) and Cl(4) ions are coordinated to 5 and 6 N atoms, respectively. In the crystal, there are two hydrogen bonds between N5A and N3B:N5B and N3A of the neighboring molecules, and constitute the major intermolecular attraction and packing force. These two molecules make a centro-symmetric dimer.

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“…A number of related structures have been published previously (e.g. Brown, 1967;Brown & Gash, 1984;Brown & Sengier, 1984). The molecular conformation of (1) (synthesized at the SPIC Science Foundation, Madras) is shown in Fig.…”

Section: Commentmentioning

confidence: 95%