Solid‐State Structure of Free Base Guanidine Achieved at Last

Yamada, Takahiro; Liu, Xiaohui; Englert, Ulli; Yamane, Hisanori; Dronskowski, Richard

doi:10.1002/chem.200900508

Cited by 70 publications

(89 citation statements)

References 23 publications

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“…13 The structure of guanidine in the solid-state was recently resolved, revealing the high tendency of this molecule to form hydrogen bond (HB) interactions. 14 Tautomerism in guanidines has been the object of a recent 15 N NMR study; 15 as have its vibrational properties, which have been the subject of a theoretical study. 16 In an attempt to elucidate their mode of binding to biological receptors, Kleinmaier et al have investigated the conformational preferences of mono-alkylated acyl guanidines.…”

Section: Introductionmentioning

confidence: 99%

Pyridin-2-yl Guanidine Derivatives: Conformational Control Induced by Intramolecular Hydrogen-Bonding Interactions

et al. 2011

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The synthesis and conformational analysis of a series of pyridin-2-yl guanidine derivatives using NMR, X-ray crystallography and B3LYP/6-31+G** theoretical studies are reported. A remarkable difference was observed in the 1 H NMR spectra of the guanidinium salts compared with their N,N'-di-Boc protected and neutral analogues. This difference corresponds to a 180° change in the dihedral angle between the guanidine/ium moiety and the pyridine ring in the salts compared to the Boc protected derivatives; a conclusion which was supported by theoretical studies, X-ray data and NMR analysis. Moreover, our data sustains the existence of two intramolecular hydrogen bonding systems: (i) between the pyridine N1 atom and the guanidinium protons in the salts and (ii) within the tert-butyl carbamate groups of the Boc protected derivatives. To verify that the observed conformational control arises from these intramolecular interactions, a new series of N-Boc-N'-propyl substituted pyridin-2-yl guanidines was also prepared and studied.

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Section: Introductionmentioning

confidence: 99%

Pyridin-2-yl Guanidine Derivatives: Conformational Control Induced by Intramolecular Hydrogen-Bonding Interactions

et al. 2011

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“…[6] The N-H bond lengths derived from SC-XRD The N1-H1 bond lengths as determined from powder neutron diffraction at T = 12 K are larger than those at 300 K. A similar finding, in this case for molecular guanidine, is even more pronounced for its N-H bond [10] and for all C-N bond lengths, too. [11] Generally, such an effect of smaller bond lengths at higher T may be attributed to a thermal motion of the rigid molecule which, however, can be verified using the data themselves by a TLS (translational, librational, and screw modes of motion) analysis. To test this hypothesis for RbCN 3 H 4 , a TLS modeling of the thermal motion was carried out using the powder neutron-diffraction data.…”

Section: Resultsmentioning

confidence: 99%

RbCN₃H₄ and CsCN₃H₄: A Neutron Powder and Single‐Crystal X‐ray Diffraction Study

Hoepfner

Jacobs

Sawinski

et al. 2013

Zeitschrift anorg allge chemie

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Abstract. Rubidium guanidinate, RbCN 3 H 4 , is the first example of a new class of compounds containing the unsubstituted guanidinate anion CN 3 H 4 -. While the first crystal-structure determination was based on powder X-ray diffraction, neutron powder and single-crystal X-ray diffraction have now been utilized to improve the previous structural model, in particular with respect to experimentally localizing the hydrogen positions, which were so far derived from density-functional

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“…In conclusion, we have synthesized the first generation of guanidine-containing pillar [5]arene that can be acidified into guanidinium-based pillar [5] …”

Section: Discussionmentioning

confidence: 99%

First Description of a Guanidine-embedded Pillar[5]arene: Opening New Avenues for Biological Applications

Xi¹,

Shaikh²,

Roosevelt³

et al. 2017

Mediterr.J.Chem.,

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Guanidine functionality embedded in macrocyclic framework provides intriguing and tunable chemical and physical characteristics to molecular structures. We describe in this paper the first example of guanidine-containing pillar[5]arene and their potential applications in biology and material science. The reaction of O-alkylated p-aminopillar[5]arene with guanylating reagent, amidinopyrazole hydrochloride, gives first ever synthesis of a new generation of guanidine-embedded pillararene 2 under mild reaction conditions.

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Solid‐State Structure of Free Base Guanidine Achieved at Last

Cited by 70 publications

References 23 publications

Pyridin-2-yl Guanidine Derivatives: Conformational Control Induced by Intramolecular Hydrogen-Bonding Interactions

Pyridin-2-yl Guanidine Derivatives: Conformational Control Induced by Intramolecular Hydrogen-Bonding Interactions

RbCN₃H₄ and CsCN₃H₄: A Neutron Powder and Single‐Crystal X‐ray Diffraction Study

First Description of a Guanidine-embedded Pillar[5]arene: Opening New Avenues for Biological Applications

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Solid‐State Structure of Free Base Guanidine Achieved at Last

Cited by 70 publications

References 23 publications

Pyridin-2-yl Guanidine Derivatives: Conformational Control Induced by Intramolecular Hydrogen-Bonding Interactions

Pyridin-2-yl Guanidine Derivatives: Conformational Control Induced by Intramolecular Hydrogen-Bonding Interactions

RbCN3H4 and CsCN3H4: A Neutron Powder and Single‐­Crystal X‐ray Diffraction Study

First Description of a Guanidine-embedded Pillar[5]arene: Opening New Avenues for Biological Applications

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RbCN₃H₄ and CsCN₃H₄: A Neutron Powder and Single‐Crystal X‐ray Diffraction Study