Crystal and molecular structure of a new biguanide metal complex, [Cu(AMNH)2]Cl2

Das, Bankim C.; Dey, Indrani; Biswas, Goutam; Banerjee, Rupendranath; Iitaka, Yōichi; Banerjee, Amitav

doi:10.1007/bf01182528

Cited by 4 publications

(4 citation statements)

References 15 publications

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“…The four alkylbiguanidium dihydrochlorides had their double bonds positioned between C1 and N1 and C2 and N5. This is different from what was previously reported for metal-coordinated biguanides . As Raczyńska et al previously reported, the protonation was favored on the imino groups, rather than the amino groups, because of the n−π conjugation .…”

Section: Resultscontrasting

confidence: 81%

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Synthesis and Characterization of Biguanide and Biguanidium Surfactants for Efficient and Recyclable Application in the Suzuki–Miyaura Reaction

Fortun

Schmitzer

2018

ACS Omega

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We report here the synthesis and thorough characterization of a new family of alkylbiguanides and alkylbiguanidium chlorides by 1 H and 13 C NMR and X-ray diffraction. Their critical micelle concentration was first determined by surface tension measurements. Hexylbiguanide was then studied as a surfactant in the micellar Suzuki–Miyaura cross-coupling reaction. The unexpected low reactivity of the system at high Pd/hexylbiguanide ratios was due to the change of the size and the shape of the aggregates, observed by transmission electron microscopy. The best catalytic activity was obtained for a 1:1 Pd/hexylbiguanide ratio for which the micellar conditions were conserved. Better results were obtained for several substrates, when compared to those previously obtained with metformin under the same reaction conditions. Higher yields and a better recyclability were obtained under micellar conditions with hexylbiguanide.

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Section: Resultscontrasting

confidence: 81%

“…This is different from what was previously reported for metal-coordinated biguanides. 24 As Raczyńska et al previously reported, the protonation was favored on the imino groups, rather than the amino groups, because of the n−π conjugation. 23 Finally, each molecule possesses two chlorides located in each plane of a guanidinium cation.…”

Section: Resultsmentioning

confidence: 93%

Synthesis and Characterization of Biguanide and Biguanidium Surfactants for Efficient and Recyclable Application in the Suzuki–Miyaura Reaction

Fortun

Schmitzer

2018

ACS Omega

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show abstract

“…On the basis of X-ray structural results, it was suggested that the six-membered ring can be described as a delocalized π-electron system. 117,118 Although a related reaction can be performed with methanol as a nucleophile at other metal centers, e.g., Cu(II) [119][120][121] and Zn(II), 122 the platinum(II) system 117 is the only one fully characterized starting from an individual cyanoguanidine starting material.…”

Section: Reactions At Platinum Centersmentioning

confidence: 99%

“…At least formally the reaction proceeds via coupling of cyclopentanone oxime (other metal-mediated oxime−nitrile couplings are given in section IV) or methanol with the electrophilically activated nitrile group of cyanoguanidine, loss of the other cyanoguanidine, and ring closure with concomitant deprotonation. On the basis of X-ray structural results, it was suggested that the six-membered ring can be described as a delocalized π -electron system. , Although a related reaction can be performed with methanol as a nucleophile at other metal centers, e.g., Cu(II) − and Zn(II), the platinum(II) system 117 is the only one fully characterized starting from an individual cyanoguanidine starting material.…”

Section: Reactions At Platinum Centersmentioning

confidence: 99%