Use of Organic Superbases and Temperature Effects for the Development of Reversible Protic Amino Acid Salts

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5 Citations (Scopus)

Abstract

Novel reversible organic salts based on amino acids in the presence of organic superbases [1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and tetramethylguanidine (TMG)] have been prepared. An optimized acid-base reaction methodology allowed the preparation of novel protic amino acid salts with improved water-solubility profiles and unexpected phase behavior. Complementary differential scanning calorimetry (DSC) and thermal H-1 NMR analysis indicated that a phase separation between water and amino acid salt occurs and that the process is reversible, depending upon temperature and the selected organic superbase. These studies open the possibility for tuning miscibility and ionicity of organic salts as well as development of reversible protic chiral ionic liquids or molten salts.
Original languageEnglish
Pages (from-to)2525-2530
JournalSynlett
Volume24
Issue number19
DOIs
Publication statusPublished - 2 Dec 2013

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Thermal effects
Salts
Amino Acids
Solubility
Ionic Liquids
Water
Phase behavior
Phase separation
Molten materials
Differential scanning calorimetry
Tuning
Nuclear magnetic resonance
Acids
Temperature

Keywords

  • amino acids
  • green chemistry
  • ionic liquids
  • cations
  • protonation

Cite this

@article{9352783d70954104905e827190429c10,
title = "Use of Organic Superbases and Temperature Effects for the Development of Reversible Protic Amino Acid Salts",
abstract = "Novel reversible organic salts based on amino acids in the presence of organic superbases [1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and tetramethylguanidine (TMG)] have been prepared. An optimized acid-base reaction methodology allowed the preparation of novel protic amino acid salts with improved water-solubility profiles and unexpected phase behavior. Complementary differential scanning calorimetry (DSC) and thermal H-1 NMR analysis indicated that a phase separation between water and amino acid salt occurs and that the process is reversible, depending upon temperature and the selected organic superbase. These studies open the possibility for tuning miscibility and ionicity of organic salts as well as development of reversible protic chiral ionic liquids or molten salts.",
keywords = "amino acids, green chemistry, ionic liquids, cations, protonation",
author = "Carrera, {Gon{\cc}alo Valente da Silva Marino} and Costa, {Alexandra M.} and {Nunes da Ponte}, {Manuel Luis Magalhaes} and Branco, {Lu{\'i}s Alexandre Almeida Fernandes Cobra}",
note = "This work was supported by Fundacao para a Ciencia e a Tecnologia (PEst-C/LA0006/2011, PTDC/CTM/103664/2008 and a postdoctoral fellowship GVSMC - SFRH/BPD/72095/2010). The authors thank Prof. Madalena Dionisio and Dr. Natalia Correia for support with the DSC analyses.",
year = "2013",
month = "12",
day = "2",
doi = "10.1055/s-0033-1339880",
language = "English",
volume = "24",
pages = "2525--2530",
journal = "Synlett",
issn = "0936-5214",
publisher = "Georg Thieme Verlag",
number = "19",

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TY - JOUR

T1 - Use of Organic Superbases and Temperature Effects for the Development of Reversible Protic Amino Acid Salts

AU - Carrera, Gonçalo Valente da Silva Marino

AU - Costa, Alexandra M.

AU - Nunes da Ponte, Manuel Luis Magalhaes

AU - Branco, Luís Alexandre Almeida Fernandes Cobra

N1 - This work was supported by Fundacao para a Ciencia e a Tecnologia (PEst-C/LA0006/2011, PTDC/CTM/103664/2008 and a postdoctoral fellowship GVSMC - SFRH/BPD/72095/2010). The authors thank Prof. Madalena Dionisio and Dr. Natalia Correia for support with the DSC analyses.

PY - 2013/12/2

Y1 - 2013/12/2

N2 - Novel reversible organic salts based on amino acids in the presence of organic superbases [1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and tetramethylguanidine (TMG)] have been prepared. An optimized acid-base reaction methodology allowed the preparation of novel protic amino acid salts with improved water-solubility profiles and unexpected phase behavior. Complementary differential scanning calorimetry (DSC) and thermal H-1 NMR analysis indicated that a phase separation between water and amino acid salt occurs and that the process is reversible, depending upon temperature and the selected organic superbase. These studies open the possibility for tuning miscibility and ionicity of organic salts as well as development of reversible protic chiral ionic liquids or molten salts.

AB - Novel reversible organic salts based on amino acids in the presence of organic superbases [1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and tetramethylguanidine (TMG)] have been prepared. An optimized acid-base reaction methodology allowed the preparation of novel protic amino acid salts with improved water-solubility profiles and unexpected phase behavior. Complementary differential scanning calorimetry (DSC) and thermal H-1 NMR analysis indicated that a phase separation between water and amino acid salt occurs and that the process is reversible, depending upon temperature and the selected organic superbase. These studies open the possibility for tuning miscibility and ionicity of organic salts as well as development of reversible protic chiral ionic liquids or molten salts.

KW - amino acids

KW - green chemistry

KW - ionic liquids

KW - cations

KW - protonation

U2 - 10.1055/s-0033-1339880

DO - 10.1055/s-0033-1339880

M3 - Article

VL - 24

SP - 2525

EP - 2530

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 19

ER -