Abstract
Piperazine-2,5-diones with the potential to manifest three chemically distinct and linearly independent intermolecular interactions were synthesized from the enantiomers of 2-amino-4-bromo-7-methoxyindan-2- carboxylic acid. Samples of enantiomerically pure, racemic, and meso piperazinediones were characterized in the solid state by X-ray crystallography. 'Ladder-like' intermolecular amide-to-amide hydrogen bonding interactions were observed in each case, establishing tape structures parallel to one crystallographic axis. The observed tape morphologies and crystal packing closely resemble that previously observed for a topographically similar tetramethoxy-piperazinedione. The results obtained demonstrate that the weak dipoles associated with the p-bromoanisole moiety play no role in determining order in the crystalline state.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 14301-14322 |
| Number of pages | 22 |
| Journal | Tetrahedron |
| Volume | 55 |
| Issue number | 50 |
| DOIs | |
| State | Published - Dec 10 1999 |
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Keywords
- Amino acids and derivatives
- Indanes
- Piperazinones
- X-Ray crystal structures
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Organic crystal engineering with piperazine-2,5-diones. 2. Crystal packing of weakly dipolar piperazinediones derived from 2-amino-4-bromo-7- methoxyindan-2-carboxylic acid. / Williams, Lawrence J.; Jagadish, B.; Lansdown, Michael G.; Carducci, Michael D.; Mash, Eugene A.
In: Tetrahedron, Vol. 55, No. 50, 10.12.1999, p. 14301-14322.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Organic crystal engineering with piperazine-2,5-diones. 2. Crystal packing of weakly dipolar piperazinediones derived from 2-amino-4-bromo-7- methoxyindan-2-carboxylic acid
AU - Williams, Lawrence J.
AU - Jagadish, B.
AU - Lansdown, Michael G.
AU - Carducci, Michael D.
AU - Mash, Eugene A
PY - 1999/12/10
Y1 - 1999/12/10
N2 - Piperazine-2,5-diones with the potential to manifest three chemically distinct and linearly independent intermolecular interactions were synthesized from the enantiomers of 2-amino-4-bromo-7-methoxyindan-2- carboxylic acid. Samples of enantiomerically pure, racemic, and meso piperazinediones were characterized in the solid state by X-ray crystallography. 'Ladder-like' intermolecular amide-to-amide hydrogen bonding interactions were observed in each case, establishing tape structures parallel to one crystallographic axis. The observed tape morphologies and crystal packing closely resemble that previously observed for a topographically similar tetramethoxy-piperazinedione. The results obtained demonstrate that the weak dipoles associated with the p-bromoanisole moiety play no role in determining order in the crystalline state.
AB - Piperazine-2,5-diones with the potential to manifest three chemically distinct and linearly independent intermolecular interactions were synthesized from the enantiomers of 2-amino-4-bromo-7-methoxyindan-2- carboxylic acid. Samples of enantiomerically pure, racemic, and meso piperazinediones were characterized in the solid state by X-ray crystallography. 'Ladder-like' intermolecular amide-to-amide hydrogen bonding interactions were observed in each case, establishing tape structures parallel to one crystallographic axis. The observed tape morphologies and crystal packing closely resemble that previously observed for a topographically similar tetramethoxy-piperazinedione. The results obtained demonstrate that the weak dipoles associated with the p-bromoanisole moiety play no role in determining order in the crystalline state.
KW - Amino acids and derivatives
KW - Indanes
KW - Piperazinones
KW - X-Ray crystal structures
UR - http://www.scopus.com/inward/record.url?scp=0033544756&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0033544756&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(99)00924-2
DO - 10.1016/S0040-4020(99)00924-2
M3 - Article
AN - SCOPUS:0033544756
VL - 55
SP - 14301
EP - 14322
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 50
ER -