Conformational effects in excited state intramolecular proton transfer of organic compounds

Uzhinov, B. M.; Khimich, M. N.

doi:10.1070/rc2011v080n06abeh004144

Cited by 60 publications

(39 citation statements)

References 15 publications

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“…In the excited state the proton may be transferred from amine group (NH) to keto group (C=O) through ESIPT process leads to the existence of both KHB and EHB forms [18][19][20][21][22][23]33]. In dual emission, the low intensity peak at 410 nm arises from the normal ketamine form and the red shifted high intensity peak at 435 nm corresponds to the stable tautomeric enolimine form.…”

Section: Electronic Emission Spectramentioning

confidence: 94%

“…This hypothesis leads to the concept of twisted intramolecular charge transfer (TICT) process. A number of reports have shown that the degree of steric hindrance plays an important role in dual emission arises from twisted intramolecular charge transfer (TICT) or excited state intramolecular proton transfer (ESIPT) process [18][19][20][21][22][23].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, crystal structure and DFT studies of a dual fluorescent ketamine: Structural changes in the ground and excited states

Latha

Balakrishnan

Neelakantan

2015

Journal of Molecular Structure

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Section: Electronic Emission Spectramentioning

confidence: 94%

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structure and DFT studies of a dual fluorescent ketamine: Structural changes in the ground and excited states

Latha

Balakrishnan

Neelakantan

2015

Journal of Molecular Structure

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“…Both phenomena are very rare; in 2004, a survey of the Cambridge crystallographic data centre yielded four hits that qualified as atropisomers and ten hits that qualified as rotamers [33]. Despite the rareness of the forms, recent reviews can be found on both rotamers[34,35] and atropisomers [36–38]…”

Section: What's In the Name?mentioning

confidence: 99%

The solid-state continuum: a perspective on the interrelationships between different solid-state forms in drug substance and drug product

Elder

Patterson

Holm

2014

Journal of Pharmacy and Pharmacology

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Objective The objective of the review is to provide an overview of the nomenclature used in the solid-state continuum and relate these to the development of drug substances and drug products. Key findings The importance of a rational approach to solid-state form selection, including integrated decision making (ensuring equal weight is given to the needs of the drug substance and the drug product), is vital for the effective development of a drug candidate. For example, how do secondary processing considerations influence the selection of drug substance solid-state form and resulting formulation, and how can drug substance solid-state form be used to optimise secondary processing? Further, the potential use of 'crystal' engineering to optimise stability, purity and optical resolutions, and the linked regulatory requirements, will be discussed. Summary The nomenclature used in the solid-state continuum, which contains a large number of different crystalline and non-crystalline forms, for example, amorphous systems, was reviewed. Further, the significant role of the drug substance within the solid oral dose form from a physicochemical perspective was covered.

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“…Excited state intramolecular proton transfer plays an important role in chemical and biological processes [1]. Six and five membered cycles with intramolecu lar hydrogen bond between O-H (or N-H) and C=O (or N≤) groups are typical of systems with ESIPT.…”

mentioning

confidence: 99%

“…Six and five membered cycles with intramolecu lar hydrogen bond between O-H (or N-H) and C=O (or N≤) groups are typical of systems with ESIPT. In aromatic systems with strong intramolecular hydrogen bonding with the hydroxy group as a proton donor (OH acids), the lifetime of ESIPT is tens of femtosec onds [1], indicating the barrierless character of the process. The scanty information about systems with intramolecular >N-H⋅⋅⋅N≤ and >N-H⋅⋅⋅O=C< hydrogen bonding (NH acids) does not allow for gen eral conclusions about the character of ESIPT in these systems.…”

mentioning

confidence: 99%

Femtosecond dynamics of excited-state intramolecular proton transfer in o-tosylaminobenzoic and o-acetylaminobenzoic acids

et al. 2013

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The dynamics of excited state intramolecular proton transfer (ESIPT) and of relaxation processes in o tosylaminobenzoic acid (TAC) and o acetylaminobenzoic acid (AAC) have been studied by femtosecond absorption spectroscopy with a time resolution of 30 fs. The ESIPT characteristic time in the TAC dimer and monomer and in AAC monomer is 50 fs. The excited product of photoinduced proton transfer in the mono mer undergoes effective radiationless deactivation with a characteristic time of 30 ps, one of the channels of which is internal rotation followed by intersystem crossing and internal conversion. The product of ESIPT in the TAC dimer deactivates preferentially into the ground state via radiative transition with a time of 291 ps. ESIPT in the AAC dimer is thermodynamically unfavorable and occurs with a low yield.

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Conformational effects in excited state intramolecular proton transfer of organic compounds

Cited by 60 publications

References 15 publications

Synthesis, crystal structure and DFT studies of a dual fluorescent ketamine: Structural changes in the ground and excited states

Synthesis, crystal structure and DFT studies of a dual fluorescent ketamine: Structural changes in the ground and excited states

The solid-state continuum: a perspective on the interrelationships between different solid-state forms in drug substance and drug product

Femtosecond dynamics of excited-state intramolecular proton transfer in o-tosylaminobenzoic and o-acetylaminobenzoic acids

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