Synthesis of heterocyclic compounds containing three contiguous hydrogen bonding sites in all possible arrangements

Murray, Thomas J.; Zimmerman, Steven C.; Kolotuchin, Sergei

doi:10.1016/0040-4020(94)00922-h

Cited by 66 publications

(45 citation statements)

References 42 publications

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“…The same is true for AAA/DDD [14][15][16][17] versus DDA/AAD [18,19] versus ADA/DAD pairs [7,8,[20][21][22]. Although the ADA and the DAD motifs are not self-complementary, their selfassociation is still possible due to rotamerism (Scheme 1) or tautomerism [23][24][25][26].…”

Section: Introductionmentioning

confidence: 91%

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NMR and quantum chemical studies on association of 2,6-bis(acylamino)pyridines with selected imides and 2,2′-dipyridylamine

et al. 2010

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Association constants of 2,6-bis(alkylcarbonylamino)pyridines (alkyl = methyl or ethyl) and their perfluoroalkyl analogues with succin-and maleimide as well as with 2,2 0 -dipyridylamine (complementary DAD and ADA hydrogen bonding motifs are responsible for formation of the associates) have been determined by NMR titrations and quantum chemical calculations. Interactions of 2,6-bis (alkylcarbonylamino)pyridines with imides differ by character from these of perfluoroalkyl analogues. Such large difference was not observed for the 2,2 0 -dipyridylamine associates. Since fluorine atoms cause carbonylamino groups to be stronger hydrogen bond donors, perfluorinated species of this type were found to be more stable. Single crystal X-ray structures of 2,6-bis(trifluoromethylcarbonylamino)pyridine and 2,6-bis(pentafluoroethylcarbonylamino)pyridine have been also determined.

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Section: Introductionmentioning

confidence: 91%

“…The 2D pulsed field z-gradient (PFG) selected 1 H, 13 C HMQC, and 1 H, 13 C HMBC experiments were run to assign reliably the 13 C NMR spectra [58]. 15 the solid titrants added equal to: 0.5-50 for 5, 1-10 for 6, and 1-20 for 7. The titration was continued to obtain the Dd(H7) smaller than 0.1 ppm upon addition of the next portion.…”

Section: Synthesismentioning

confidence: 99%

NMR and quantum chemical studies on association of 2,6-bis(acylamino)pyridines with selected imides and 2,2′-dipyridylamine

et al. 2010

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“…6 Starting with 1, aminolysis followed by the conversion of the cyano group into the carbaldehyde gave 2,6-diamino-3,5-pyridinedicarboxaldehyde 3, which then underwent the condensation reaction with 2-acetylpyridine to give the desired anthyridine ligand 4. Compound 4 was characterized by NMR spectroscopy.…”

Section: Results and Discussion Preparation And Characterization Of Cmentioning

confidence: 99%

Ruthenium Complexes with an Anthyridine‐based Ligand. Synthesis, Characterization and Catalytic Activity

Liu

Peng

et al. 2013

J Chinese Chemical Soc

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“…This effect was first recognized by Jorgensen and Pranata, 12 and was experimentally verified by Murray and Zimmerman. 13 Since these early studies, Murray et al 11 have analyzed a variety of hydrogen bonding patterns, which in general verify the concept. We were interested in further probing secondary hydrogen bonding by forming a host-guest complex that possesses a cationic hydrogen bond donor.…”

Section: Secondary Hydrogen Bonding Arraysmentioning

confidence: 95%

“…6,11 The binding strength of the complexes is dependent not only upon the number of hydrogen bonds, but also upon the arrangement of the hydrogen bonds. For example, arranging either hydrogen bond donors or acceptors on the same molecule results in stronger binding than if the donors and acceptors are intermingled on the same molecule.…”

Section: Secondary Hydrogen Bonding Arraysmentioning

confidence: 99%

NON-AQUEOUS TITRATIONS AS A TOOL IN THE STUDY OF MOLECULAR RECOGNITION PHENOMENA. USES IN DISTINGUISHING HYDROGEN BONDING FROM PROTON TRANSFER, THE MEASUREMENT OF COMPLEX INDUCED pKa SHIFTS, AND THE ABILITY TO DISTINGUISH THE CATALYTIC ROLES OF GENERAL ACIDS AND BASES

Hannon

Bell

Kelly-Rowley

et al. 1997

J. Phys. Org. Chem.

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Whenever hydrogen bonding is involved in molecular recognition, the possibility of a proton transfer from the donor to the acceptor arises. In most cases the pK a of the donor is far enough above the pK a of the conjugate acid of the acceptor for it to be clear that no proton transfer will occur. However, as the difference between the donor and acceptor pK a s decreases, it can become difficult to predict whether a proton transfer will occur. Since most hydrogen bond-driven molecular recognition is studied in low dielectric solvents, non-aqueous titrations can be used to measure the pK a s and therefore predict proton transfers. In this paper three studies which involved non-aqueous titrations are summarized. The first deals with distinguishing simple proton transfer from host-guest complex formation. The second involves measuring pK a shifts upon host-guest complex formation. The last is a study of the catalysis of a phosphoryl transfer. In all three scenarios the non-aqueous titration method gave results which would have been difficult to obtain by other means, and which proved crucial for a complete understanding of the molecular recognition process.

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Synthesis of heterocyclic compounds containing three contiguous hydrogen bonding sites in all possible arrangements

Cited by 66 publications

References 42 publications

NMR and quantum chemical studies on association of 2,6-bis(acylamino)pyridines with selected imides and 2,2′-dipyridylamine

NMR and quantum chemical studies on association of 2,6-bis(acylamino)pyridines with selected imides and 2,2′-dipyridylamine

Ruthenium Complexes with an Anthyridine‐based Ligand. Synthesis, Characterization and Catalytic Activity

NON-AQUEOUS TITRATIONS AS A TOOL IN THE STUDY OF MOLECULAR RECOGNITION PHENOMENA. USES IN DISTINGUISHING HYDROGEN BONDING FROM PROTON TRANSFER, THE MEASUREMENT OF COMPLEX INDUCED pKa SHIFTS, AND THE ABILITY TO DISTINGUISH THE CATALYTIC ROLES OF GENERAL ACIDS AND BASES

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