<sup>13</sup>C Nuclear Magnetic Resonance Spectra of Poly(N-formylpropylenimine) and Some Related Formamide Derivatives

Hamilton, James G.; Ivin, K. J.; Kuan-Essig, L. C.; Watt, P.

doi:10.1021/ma60049a012

Cited by 13 publications

(5 citation statements)

References 7 publications

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“…The pattern observed is similar to patterns reported in 13 C NMR spectra of amides and is ascribed to a distribution of rotational conformers ( − ). Analogous rotational isomerism has been observed in formamidopyrimidine derivatives of dGuo ( , ).…”

Section: Resultssupporting

confidence: 85%

A 2-Iminohydantoin from the Oxidation of Guanine

Sangaiah²,

Degen³

et al. 2006

Chem. Res. Toxicol.

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The nucleobase guanine was oxidized with dimethyldioxirane (DMDO) to explore the role of epoxidizing agents in oxidative DNA damage. Treatment of guanine with 10% molar excess DMDO in aqueous solution at 0 degrees C and pH 7.5 followed by workup under mild conditions gave 5-carboxamido-5-formamido-2-iminohydantoin (1) as the sole isolable product in 71% yield. The structure of 1 was established on the basis of mass spectrometry and NMR studies on 1 and its isotopomers generated by the oxidation of [4-(13)C] and [7-(15)N]guanine, which yield [5-(13)C]1 and [7-(15)N]1. The distribution of 13C and 15N labels in the isotopomeric products supports initial epoxidation of the C4-C5 bond of guanine followed by a 1,2-acyl migration of guanine C6. Compound 1 is suggested as a possible primary DNA lesion from putative epoxidizing agents, including hydroperoxides present during biological processes such as lipid peroxidation.

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Section: Resultssupporting

confidence: 85%

A 2-Iminohydantoin from the Oxidation of Guanine

Sangaiah²,

Degen³

et al. 2006

Chem. Res. Toxicol.

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“…The chemical shifts of the two CH 2 groups in each structure will obviously depend on the type of formamide (mono‐ or di‐ N ‐substituted) and on whether the neighbouring amino groups are secondary or tertiary. In addition it must be recognised22 that, as is well known for small amides, the formamide groups have a planar conformation because of the partial double‐bond character of the NCO bond and that at ambient temperature rotation about this bond is slow on the NMR timescale, resulting in two non‐equivalent rotational isomers for an N ‐alkyl amide and two distinct peaks for both carbons in syn and anti CH 2 CH 2 N units in an N , N ‐dialkyl amide. Thus up to 20 peaks might be expected for all CH 2 carbons in Scheme .…”

Section: Resultsmentioning

confidence: 99%

Assignment of ¹H NMR spectrum and investigation of oxidative degradation of poly(ethylenimine) using ¹H and ¹³C 1‐D and 2‐D NMR

Idris

Mkhatresh

Heatley

2006

Polymer International

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The 1 H NMR spectrum of poly(ethylenimine) (PEI) has been assigned using two-dimensional NMR correlation with the previously established assignment of the 13 C spectrum. The oxidative thermal and UV degradation of PEI has been studied using mass loss measurements, and NMR and Fourier transform infrared spectroscopy. Analysis of the spectra of the degradation products shows that the degradation process may readily be monitored, particularly by 13 C NMR. The major products are formamide and other amide groups which may be understood in terms of chain scission and dehydration reactions of hydroperoxides.

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“…Polymerization cationic initiator gives poly(JV-[p-(substituted) benzoyl]ethylenimine) (2) as already known.1 Table I shows the polymerization results of the five monomers (la-e) and some data for the resulting polymers (2a-e). All these polymers are white powdery materials except for 2e, which is a pale-yellow powder.…”

Section: Resultsmentioning

confidence: 65%

“…The copolymer structure, however, did not change and the OZO/SAn composition of the copolymers was 2:1 in all cases (no. [1][2][3][4][5][6] in Table I).…”

Section: Resultsmentioning

confidence: 99%

Spontaneous 2:1 sequence-regulated copolymerization of cyclic imino ethers with cyclic carboxylic anhydrides

Kobayashi¹,

Isobe²,

Saegusa³

1982

Macromolecules

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The present paper reports copolymerizations of two cyclic imino ethers, 2-oxazoline (OZO) and 5,6-dihydro-4£f-1,3-oxazine (OZI), with two cyclic carboxylic anhydrides, succinic anhydride (SAn) and glutaric anhydride (GAn). The copolymerizations took place spontaneously around room temperature to 100 °C to produce 2:1 sequence-regulated copolymers (1). This result was explained by the concept of "no catalyst alternating copolymerization via zwitterion intermediate". Thus, OZO and OZI behaved as nucelophilic monomers (Mn) whereas SAn and GAn acted as electrophilic monomers (ME). First, a 1:1 bicyclic adduct (such as 3, 6, and 7) is formed by the reaction between MN and ME. Then the cyclic adduct behaved as ME to react with another molecule of MN, giving rise to a zwitterion like 5, a key intermediate for the copolymerization, which has a 2:1 MN/ME composition. Subsequent reactions of these key intermediates led to the production of 2:1 sequence-regulated copolymers 1.

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¹³C Nuclear Magnetic Resonance Spectra of Poly(N-formylpropylenimine) and Some Related Formamide Derivatives

Cited by 13 publications

References 7 publications

A 2-Iminohydantoin from the Oxidation of Guanine

A 2-Iminohydantoin from the Oxidation of Guanine

Assignment of ¹H NMR spectrum and investigation of oxidative degradation of poly(ethylenimine) using ¹H and ¹³C 1‐D and 2‐D NMR

Spontaneous 2:1 sequence-regulated copolymerization of cyclic imino ethers with cyclic carboxylic anhydrides

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13C Nuclear Magnetic Resonance Spectra of Poly(N-formylpropylenimine) and Some Related Formamide Derivatives

Cited by 13 publications

References 7 publications

A 2-Iminohydantoin from the Oxidation of Guanine

A 2-Iminohydantoin from the Oxidation of Guanine

Assignment of 1H NMR spectrum and investigation of oxidative degradation of poly(ethylenimine) using 1H and 13C 1‐D and 2‐D NMR

Spontaneous 2:1 sequence-regulated copolymerization of cyclic imino ethers with cyclic carboxylic anhydrides

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¹³C Nuclear Magnetic Resonance Spectra of Poly(N-formylpropylenimine) and Some Related Formamide Derivatives

Assignment of ¹H NMR spectrum and investigation of oxidative degradation of poly(ethylenimine) using ¹H and ¹³C 1‐D and 2‐D NMR