sara galal - 4-3-2017 at 05:17
can amide group undergoes oxidation with hydrogen peroxide at room temperature to yield nitro group ??
if yes what is the suggested mechanism?? as i added 0.5 ml of hydrogen peroxide (30 %) to 10 ml aqueous solution of amino acids containing structure
left it at room temperature for 72 hours , then freeze dried the aqueous solution and analysed the resullted solid by IR, the IR frequencies showed
two new strong bands at 1587.42 and 1398.36 than the IR of the intact structure before oxidation, thanks in advance
NitratedKittens - 4-3-2017 at 05:29
Do you mean amine or amide
sara galal - 4-3-2017 at 05:41
amide group, this is the trick i am trying to oxidize amino acids containing structure
JnPS - 4-3-2017 at 07:57
Amides are not very reactive. I have never heard of it being possible to oxidize them to a nitro group. The only real reactions I know of for amides
are hydrolysis and reductions. That's not to say it isn't possible they undergo other reactions, they probably do; my nitrogen chemistry isn't very
extensive. You mean to say you tried oxidizing a solution of glutamine and/or asparagine with peroxide? Maybe the amine group on them oxidized to a
nitro group? Even that is speculative.
sara galal - 4-3-2017 at 09:24
my structure is a peptide chain of a sequence of amino acids of arginine- glycine-aspartic acid- tryptophan-proline-cysteine-mercaptopropionic acid
linked together with amide linkage and disulphide bridge, the IR chart showing a very broad band at 3435.22 corresponding i think to N-H and OH
stretch of amide group and carboxylic acids of amino acids and C-H stretch of alkane ,but the change that happened in the IR chart is the appearance
of two broad strong bands at 1587.42 and 1398.36(less broad than the band at 1587) than the IR of the intact structure before oxidation, i first
thought of oxidation of the disulphide bond to sulphoxide, sulphone or even sulphonic acid(unfortunately, i am not an organic chemistry expert, i just
came with this problem during my research)but i looked at the IR frequencies table and found that the frequencies of sulphoxide at 1030-1070 cm-1,
sulphone 1325 and 1140 cm and even sulphonic acid at 1345 and 1150 cm-1 so i excluded the oxidation of the disulphide bond as it shouldnot transmit at
1587cm-1 as i found in IR frequency tables, also there is a small shoulder at 1251 cm-1, so i thought about oxidation of N-H of amide groups to nitro
containing derivatives as i found two strong broad band at 1587 &1399 cm-1 but of course didn't know is it possible under these conditions or
not,lso i did LC-MS analysis of my oxidized product by LC-MS ESI, without fragmentation it gave m/z smaller than the m/z of the intact structure which
suggeste certain cleavage of bonds but where and how ,i am still searching for the answer