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

Gonçalo Valente da Silva Marino Carrera; Alexandra M. Costa; Manuel Luis Magalhaes Nunes da Ponte; Luís Alexandre Almeida Fernandes Cobra Branco

doi:10.1055/s-0033-1339880

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

Gonçalo Valente da Silva Marino Carrera, Alexandra M. Costa, Manuel Luis Magalhaes Nunes da Ponte, Luís Alexandre Almeida Fernandes Cobra Branco

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	2525-2530
Journal	Synlett
Volume	24
Issue number	19
DOIs	https://doi.org/10.1055/s-0033-1339880
Publication status	Published - 2 Dec 2013

Keywords

amino acids
green chemistry
ionic liquids
cations
protonation

Access to Document

10.1055/s-0033-1339880Licence: CC BY

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{\c c}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 = dec,

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",

}

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

SN - 0936-5214

VL - 24

SP - 2525

EP - 2530

JO - Synlett

JF - Synlett

IS - 19

ER -

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

Abstract

Keywords

Access to Document

Fingerprint

Cite this