Ian Cunningham

Dr Ian Cunningham


Senior Lecturer in Chemistry
+44 (0)1483 686832
05 AZ 03
Executive Assistant: Linda Bennett

Academic and research departments

School of Chemistry and Chemical Engineering.

About

University roles and responsibilities

  • Former Head of Chemistry
  • Athena SWAN Lead

    Previous roles

    2019 - 2022
    Head of Department of Chemistry
    University of Surrey

    Affiliations and memberships

    CChem FRSC
    Chartered Chemist and Fellow of the Royal Society of Chemistry

    Research

    Research interests

    Teaching

    Publications

    Stephen Maddocks, Nurul F. Samuri, Katerina Ridge, Ian D. Cunningham, William J. S. Lockley (2023)Benzylic deuteration of alkylnitroaromatics via amine-base catalysed exchange with deuterium oxide, In: Journal of labelled compounds & radiopharmaceuticals66(1)11pp. 11-21 Wiley

    This paper describes the deuterium-labelling of alkylnitroaromatics by base-catalysed exchange with deuterium oxide. As the alkyl protons alpha to the aromatic ring are the most acidic sites in the molecule, regioselective hydrogen isotope exchange at this benzylic location leads to a regiospecifically deuterated product. The exchange labelling takes place in good yields and with high atom% abundance in the presence of an appropriate nitrogen base. Alkylated 2,4-dinitrobenzenes deuterate at room temperature under catalysis by triethylamine, whilst alkylated 2-nitro- or 4-nitrobenzenes and related mono-nitroaromatics require higher temperatures and catalysis by 1,5-diazobicyclo[4.3.0]non-5-ene (DBN). The labelling reactions require an inert gas atmosphere, but otherwise are simple and high yielding with no obvious byproducts. Those compounds in which the benzylic protons are in an ortho-orientation with respect to the nitro group label somewhat more slowly than the analogues where there is a para relationship. In addition, higher alkyl homologues undergo benzylic deuteration at slower rates than methyl.

    Ian D. Cunningham, Katerina Ridge, William Lockley, Peter Jenkins, Edward D. McNaghten, Neil Seagrave (2019)Ageing mechanisms of nitroethylbenzenes, In: Journal of energetic materials37(2)pp. 188-198 Taylor & Francis

    Simulated ageing of 2,4-dinitro-1-ethylbenzene (DNEB) in DMSO in the presence of O2 in a closed system at 85–105°C gave benzylic oxidised products 1-(2,4-dinitrophenyl)ethanol (DNPE) and 2,4-dinitroacetophenone (DNAP), with the latter as the major product. Evidence for the formation of 3-methyl-6-nitro-2,1-benzoisoxazole (an ‘anthranil’), suggested in the literature as a likely decomposition product, is scant. A mechanism with initial H-abstraction to yield an electron-rich benzylic radical as the rate-limiting step is suggested, supported by a small kinetic isotope effect kH/kD ~2 and a reactivity in the order 2,4,6-trinitro-1-ethylbenzene TNEB > DNEB > 4-nitro-1-ethylbenzene (NEB). The activation energy for DNEB oxidation is 40 kJ mol−1, a value that translates to 1% oxidative decomposition of DNEB after ~ 14 d under an O2 atmosphere, or 70 d in air at ambient temperature.

    ID Cunningham, A Basaleh, HA Gazzaz (2012)Pre-steady state reactivity of 5,10,15,20-tetrakis(pentafluorophenyl)-21H,23H-porphyrin iron(III) chloride with hydrogen peroxide, In: Dalton Transactions: an international journal of inorganic chemistry
    ID Cunningham, TN Danks, JN Hay, I Hamerton, S Gunathilagan, C Janczak (2002)Stability of various metalloporphyrin catalysts during hydrogen peroxide epoxidation of alkene, In: JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL185(1-2)PII S1381-pp. 25-31 ELSEVIER SCIENCE BV
    ID Cunningham, SJ Coles, MB Hursthouse (2000)Total spontaneous resolution of a cyanoguanidine showing only conformational chirality, In: CHEMICAL COMMUNICATIONS(1)pp. 61-62 ROYAL SOC CHEMISTRY
    ID CUNNINGHAM, JL BACHELOR, JM PRATT (1991)KINETIC-STUDY OF THE H2O2 OXIDATION OF PHENOLS, NAPHTHOLS AND ANILINES CATALYZED BY THE HEME OCTAPEPTIDE MICROPEROXIDASE-8, In: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2(11)pp. 1839-1843 ROYAL SOC CHEMISTRY
    ID CUNNINGHAM, J LLOR, L MUNOZ (1992)CHEMISTRY OF AMIDINES .3. ANALYSIS OF CONFORMATION ABOUT THE N'-PYRIDYL BOND IN N'-(2-PYRIDYL)FORMAMIDINES, In: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2(3)pp. 331-332 ROYAL SOC CHEMISTRY
    ID CUNNINGHAM, GJ BUIST, S ARKLE (1991)CHEMISTRY OF ISOCYANIDES .2. NUCLEOPHILIC-ADDITION OF HYDROXIDE TO AROMATIC ISOCYANIDES IN AQUEOUS DIMETHYL-SULFOXIDE - CORRELATIONS OF RATE WITH A NUCLEOPHILICITY FUNCTION, In: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2(5)pp. 589-593 ROYAL SOC CHEMISTRY
    ID CUNNINGHAM, J LLOR, L MUNOZ (1991)CHEMISTRY OF AMIDINES .2. SUBSTITUENT AND SOLVENT EFFECTS OF ROTATIONAL BARRIERS IN N'-PYRIDYLFORMAMIDINES, In: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2(11)pp. 1751-1753 ROYAL SOC CHEMISTRY
    ID Cunningham, K Fassihi (2005)Kinetics and mechanism of methyl acrylate homo- and co-polymerisation catalysed by cyclopentadienyltitanium trichloride-MAO, In: JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL232(1-2)pp. 187-192 ELSEVIER SCIENCE BV
    ID CUNNINGHAM, JS BLANDEN, J LLOR, L MUNOZ, AP SHARRATT (1991)CHEMISTRY OF AMIDINES .1. DETERMINATION OF THE SITE OF INITIAL PROTONATION IN N'-PYRIDYLFORMAMIDINES, In: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2(11)pp. 1747-1750 ROYAL SOC CHEMISTRY
    ID Cunningham, V Crawley (2009)Catalysis of the Diels-Alder reaction by solids, In: JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL301(1-2)pp. 47-51 ELSEVIER SCIENCE BV
    ID Cunningham, JP Courtois, TN Danks, DM Heyes, DJ Moreton, SE Taylor (2003)Synthesis and characterisation of calixarene-stabilised calcium carbonate overbased detergents, In: COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS229(1-3)pp. 137-147 ELSEVIER SCIENCE BV
    ID Cunningham, BG Cox, NC Wan, DC Povey, GW Smith (1999)Acidity and N-methylation of N-aryl-N '-cyanoguanidines, In: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2(4)pp. 693-697 ROYAL SOC CHEMISTRY
    ID Cunningham, NC Wan (1996)C-13 and N-15 NMR study of electron distribution in N-aryl-N'-cyanoguanidines, In: MAGNETIC RESONANCE IN CHEMISTRY34(3)pp. 221-226 JOHN WILEY & SONS LTD
    ID Cunningham, NC Wan, DC Povey, GW Smith, BG Cox (1997)N-cyano-N'-(4-methoxyphenyl)guanidine, In: ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS53pp. 984-985 MUNKSGAARD INT PUBL LTD
    ID Cunningham, TN Danks, JN Hay, I Hamerton, S Gunathilagan (2001)Evidence for parallel destructive, and competitive epoxidation and dismutation pathways in metalloporphyrin-catalysed alkene oxidation by hydrogen peroxide, In: TETRAHEDRON57(31)pp. 6847-6853 PERGAMON-ELSEVIER SCIENCE LTD
    ID Cunningham, A Brownhill, I Hamerton, BJ Howlin (1997)The ene reaction between maleimides and allyl-substituted aromatics, In: TETRAHEDRON53(39)pp. 13473-13494 PERGAMON-ELSEVIER SCIENCE LTD
    ID CUNNINGHAM, GR SNARE (1992)IDENTIFICATION OF CATALYTIC PATHWAYS IN THE PEROXIDATIC REACTIONS OF THE HEME OCTAPEPTIDE MICROPEROXIDASE-8, In: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2(11)pp. 2019-2023 ROYAL SOC CHEMISTRY
    ID Cunningham, K Bhaila, DC Povey (2013)Computational calculation of absolute aqueous pK(a) values for phenols, In: COMPUTATIONAL AND THEORETICAL CHEMISTRY1019pp. 55-60 ELSEVIER SCIENCE BV
    ID Cunningham, J-P Courtois, TN Danks, DM Heyes, DJ Moreton, SE Taylor (2007)Evidence for a fragmentation mechanism during the formation of calcium carbonate organo-nano-particles, In: COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS301(1-3)pp. 184-188 ELSEVIER SCIENCE BV
    ID Cunningham, M Woolfall (2005)Deprotonation of calixarenes in acetonitrile, In: JOURNAL OF ORGANIC CHEMISTRY70(23)pp. 9248-9256 AMER CHEMICAL SOC
    ID CUNNINGHAM, JL BACHELOR, JM PRATT (1994)PEROXIDATIC ACTIVITY OF HEME OCTAPEPTIDE COMPLEXES WITH ANILINES, NAPHTHOLS AND PHENOLS, In: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2(6)pp. 1347-1350 ROYAL SOC CHEMISTRY
    ID Cunningham, ME Light, MB Hursthouse (1999)N-(4-Chlorophenyl)-N-methylcyanamide, In: ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS55pp. 1833-1835 MUNKSGAARD INT PUBL LTD
    ID CUNNINGHAM, NC WAN, BG COX (1994)H-1 AND N-15 NMR-STUDIES OF N-SUBSTITUTED-N'-CYANOGUANIDINES, In: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2(8)pp. 1849-1853 ROYAL SOC CHEMISTRY
    ID CUNNINGHAM, A BROWNHILL, I HAMERTON, BJ HOWLIN (1994)KINETICS AND MECHANISM OF THE TITANIUM TETRACHLORIDE-CATALYZED CYCLOTRIMERIZATION OF ARYL CYANATES, In: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2(9)pp. 1937-1943 ROYAL SOC CHEMISTRY
    ID Cunningham, TN Danks, KTA O'Connell, PW Scott (1999)Kinetics and mechanism of the hydrogen peroxide oxidation of a pentafluorophenyl-substituted iron(III) porphyrin, In: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2(10)pp. 2133-2139 ROYAL SOC CHEMISTRY
    ID Cunningham, TN Danks, KTA O'Connell, PW Scott (1999)Metalloporphyrin-catalyzed oxidation of 2-cycloalkyl-3-hydroxynaphthoquinones, In: JOURNAL OF ORGANIC CHEMISTRY64(20)pp. 7330-7337 AMER CHEMICAL SOC
    RJ Abraham, MH Abraham, ID Cunningham (2002)Perkin questions, In: CHEMISTRY IN BRITAIN38(6)pp. 22-22 ROYAL SOC CHEMISTRY
    A BROWNHILL, ID CUNNINGHAM, I HAMERTON, BJ HOWLIN (1994)AN INVESTIGATION INTO THE CYCLOTRIMERIZATION MECHANISM OF ARYL CYANATE ESTERS, In: ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY208pp. 438-PMSE AMER CHEMICAL SOC

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