Daniel G. McCarthy

Lecturer In Organic Chemisrty
Chemistry

T: 353 (0)21 490-2449
F: 353 (0)21 490-4097
E: d.mccarthy@ucc.ie

Dr. Dan McCarthy is from Bandon, Co. Cork where he attended Saint Patrick's National School and Hamilton High School. He graduated from U.C.C. with an honours B.Sc. in Chemistry in 1974 and subsequently carried out postrgraduate work, at U.C.C., in the area of physical orgaic chemisrty with Professor A.F. Hegarty and was awarded the Ph.D. degree in 1978. He was awarded an NUI travelling Studentship and an 1851 Scholarship and carried out postdoctoral research work in heterocyclic chemistry at Imperial College of Science and Technology, London, with Professor C.W. Rees for two years before rerturning to U.C.C. in 1980 as a College Lecturer in organic chemisrty. He is involved in research and teachingof organic chemisrtyand spectroscopy and in the supervision of the departments NMR service  

Research Interests

The research that I have conducted is close to the mainstream of organic chemistry and involves a selected group of topics of interest and importance which have links to pharmaceuticals and materials. Synthesis and synthetic methodology are cornerstone techniques for my research in the areas of heterocyclic chemistry, organic nitrogen functional groups, organic sulphur and selenium reagents, transition metal catalysts, investigation of reaction mechanisms using the techniques of physical organic chemistry (largely solution phase kinetics) and providing substrates for projects in the biotransformations of organic compounds( in conjunction with Professor Maguire).

Using synthetic chemistry as a basis and in conjunction with a group of capable, enthusiastic and highly motivated graduate students, efficient syntheses of a wide range of 3(2H)-furanones and their 4,5-dihydroderivatives has been achieved - some of this work has incorporated the use of Pd(0)-mediated C-C bond forming reactions on bromo-and iodofuranones. The process facilitated an extension to synthetic endeavours for the preparation of 4-fluoro-3(2H)-furanones. These heterocycles are of importance in the pharmaceutical area because methods for the efficient introduction of fluorine can be employed in the synthesis of 18F-labelled materials for use with PET, an imaging technique with important medical applications.

Our interest in the chemistry of organic nitrogen functional group chemistry has concentrated on two groups of heterocumulenes: ketenimines and isocyanates. Development of chemistry involving the addition of electrophilic sulphur and selenium reagents and organometallic reagents to ketenimines has been an important contribution to the chemistry of these compounds. Serendipity contributed to discovery of a new synthesis of isocyanates from isocyanides and formamides. This chemistry has the potential to become a standard isocyanate synthesis.

Biotransformations of small organic molecules - 4,5-dihydrofuranonnes, have provided an opportunity to carry out fundamental research on the asymmetric synthesis of hydroxytetrahydrofurans of pharmacological interest, e.g. muscarine and its analogues. Development of expertise in t his area should foster increased interactions with the Irish pharmaceutical and fine chemical industry which is now set to embrace biotechnology based processes on a significant scale.

In addition to their use for molecular structure determination and verification on a routine basis, we have used the most important of the techniques, NMR spectroscopy, to investigate the kinetics and mechanisms of reactions in solution such as the rearrangement of acylated 1-hydroxy-benzotriazole. This is a long standing scientific problem of relevance to the well known N,N-dicyclohexylcarbodi-imide (DCC) mediated method of peptide synthesis.

Our research with heterocycles has discovered a group of compounds with novel photoluminescence properties. Compounds with these properties have well known applications in the materials science as components of light emitting diodes - OLEDs and WOLEDs.

In addition to my research activities I play a very significant role (~25% of my time) as Director of the NMR Spectroscopy Service in UCC. Currently we have a total of four high field NMR spectrometers between Chemistry and the ABCRF - 300, 400, 500 and 600MHz, and provide a service to ~50 researchers within Chemistry plus external users from the pharmaceutical industry (8 companies), Teagasc, CIT and other occasional users such as UL. The UCC NMR service is unique among the third level institutions in complying with regulatory and quality standards required by the pharmaceutical sector. The strategic importance of this technical service to the local pharmachem sector is widely recognised.


Employment

 EmployerPositionFrom / To
Imperial College of Science and Technology London Postdoctoral Research Fellow/
University College Cork Lecturer in Organic Chemisrty/
University College Cork Ph.D Researcher/

Education

 YearInstituionQualificationSubject
1978University College Cork PHDChemistry
1974University College Cork B.Sc. (Honours)Chemistry