
TY  - JOUR
A1  - Latif, Tariq 
A1  - Javed, Tariq 
A1  - Lynch, Daniel E. 
A1  - Pryce, Robert J. 
A1  - Byriel, Karl A. 
T1  - X-Ray Crystal Structure of <emph type="2">N</emph>-[3-(Diethylaminomethyl)-4- hydroxyphenyl]acetamide and its Hydrochloride Salt. Two Forms of an Important Precursor in the Synthesis of Anti-Tuberculosis Drugs
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1999
VL  - 52
IS  - 9
SP  - 909
EP  - 913
KW  - 
UR  - https://doi.org/10.1071/CH99040 
N2  - N-&#91;3-(Diethylaminomethyl)-4-hydroxyphenyl&#93;acetamide (dmhpa) and its hydrochloride salt (dmhpaH+ Cl&#8722;) have been prepared and their X-ray crystal structures determined. The structure of dmhpa comprises an intramolecular hydrogen bond between the hydroxy group and the diethylaminomethyl nitrogen and an intermolecular association between adjacent N-acetamide groups resulting in a non-centrosymmetric interdigitated &#8216;V&#8217; polymeric network. Quantitative non-linear optical measurements on a powdered sample of dmhpa revealed a second harmonic signal of two-thirds the intensity of a urea standard. In contrast, the hydrochloride salt is formed via protonation of the diethylaminomethyl nitrogen and resides in a complex hydrogen-bonded network which involves not only the free chloride ion but also one water molecule per dmhpaH+ Cl&#8722;. 
ER  -

