(Last updated 11 November 2024)
Figure . The molecular diagram of Phloroglucinol.
Phloroglucinol was studied by Doris Braun as part of a series of compounds which have hydrate and anhydrate crystal structures.
| REFCODE | PHGLOL |
|---|---|
| Formula | C6 H6 O3 |
| Common Name | Phloroglucinol |
| IUPAC Systematic Name | 1,3,5-trihydroxybenzene |
| CSD Refcodes | PHGLOL01 |
| Search Identifier | A |
| Scientist | Doris Braun |
| Date | 2012 |
| Publication | Braun DE, Tocher DA, Price SL, Griesser UJ 2012. The Journal of Physical Chemistry B 116, 3961-3972. DOI: Open paper (10.1021/jp211948q) |
| Energy Model | 1 |
| Study_ID | 20 |
| Programs | Rigid CrystalPredictor, DMACRYS (2.0.2) |
| Location on S Drive | \\CHEMISTRY_CPOSS\\Phloroglucinol\\Phloroglucinol_CP |
| Potential Description | CrystalPredictor GDMA2 (MP2/6-31G(d,p)) + FIT |
| Energy Model | 2 |
| Study_ID | 11 (published) |
| Programs | Study_ID=20, DMAflex (2.0), DMACRYS (1.1.1) |
| Location on S Drive | \\CHEMISTRY_CPOSS\\Phloroglucinol\\Phloroglucinol_CO |
| Potential Description | CrystalOptimizer GDMA2 (MP2/6-31G(d,p)) + FIT |
| Scientist | Louise Price |
| Date | January 2024 |
| Energy Model | 2a |
| Study_ID | 12 |
| Programs | Study_ID=20, CrystalOptimizer (2.4.7.1), DMACRYS (2.3.1.1) |
| Location on S Drive | \\CHEMISTRY_CPOSS\\Phloroglucinol\\Phloroglucinol_CO2 |
| Potential Description | CrystalOptimizer GDMA2 (MP2/6-31G(d,p)) + FIT |
| Energy Model | 3 |
| Study_ID | 30 |
| Programs | Study_ID=12, DMACRYS (2.3.1.1), BZ-averaged props |
| Location on S Drive | \\CHEMISTRY_CPOSS\\Phloroglucinol\\Phloroglucinol_PCM |
| Potential Description | GDMA2.2(PCMdielectric3(MP2/6-31G(d,p))) + FIT |
| REFCODE | PHGLOH |
| Formula | C6 H6 O3 - 2(H2 O1) |
| Common Name | Phloroglucinol dihydrate |
| IUPAC Systematic Name | 1,3,5-trihydroxybenzene dihydrate |
| CSD Refcodes | PHGLOH02 (proton disordered) |
| Search Identifier | B |
| Scientist | Doris Braun |
| Date | 2012 |
| Publication | Braun DE, Tocher DA, Price SL, Griesser UJ 2012. J. Phys. Chem. B 116, 3961-3972. DOI: Open paper (10.1021/jp211948q) |
| Energy Model | 1 |
| Study_ID | 20 |
| Programs | Rigid CrystalPredictor (unknown), DMACRYS (2.0.2) |
| Location on S Drive | \\CHEMISTRY_CPOSS\\Phloroglucinol\\Phloroglucinoldihydrate_CP |
| Potential Description | CrystalPredictor GDMA2 (MP2/6-31G(d,p)) (PBE1PBE/aug-cc-pvtz for water) + FIT |
| Energy Model | 2 |
| Study_ID | 10 |
| Programs | Study_ID=20, DMAflex (2.0), DMACRYS (1.1.1) |
| Location on S Drive | \\CHEMISTRY_CPOSS\\Phloroglucinol\\Phloroglucinoldihydrate_CO |
| Potential Description | CrystalOptimizer GDMA2 (MP2/6-31G(d,p)) + FIT |
Figure . Crystal energy landscape of (left) phloroglucinol and (right) phloroglucinol dihydrate from previous work.
Table . Crystallographic information for CSD entries for phloroglucinol. Different forms (including hydrates) are coloured differently.
| REFCODE | space group | Z’ | a / Å | b / Å | c / Å | α / ° | β / ° | γ / ° | density / g cm-3 | Form |
|---|---|---|---|---|---|---|---|---|---|---|
| PHGLOH | Pnma | 0.5 | 6.73 | 13.58 | 8.09 | 90 | 90 | 90 | 1.457 | Dihydrate |
| PHGLOH01 | Pnma | 0.5 | 6.5841 | 13.5128 | 8.0382 | 90 | 90 | 90 | 1.506 | Dihydrate |
| PHGLOH02 | Pnma | 0.5 | 6.5942 | 13.5455 | 8.0423 | 90 | 90 | 90 | 1.499 | Dihydrate |
| PHGLOH03 | Pnma | 0.5 | 6.5876 | 13.517 | 8.0345 | 90 | 90 | 90 | 1.505 | Dihydrate |
| PHGLOH04 | Pnma | 0.5 | 6.6209 | 13.5606 | 8.0462 | 90 | 90 | 90 | 1.491 | Dihydrate |
| PHGLOL | P212121 | 1 | 4.83 | 9.37 | 12.56 | 90 | 90 | 90 | 1.474 | I |
| PHGLOL01 | P212121 | 1 | 4.7778 | 9.3581 | 12.4433 | 90 | 90 | 90 | 1.506 | I |
Table . Experimental information for CSD entries for phloroglucinol and phloroglucinol dihydrate.
| REFCODE | space group | R factor | T / K | Year | Comments |
|---|---|---|---|---|---|
| PHGLOH | Pnma | 23 | 295 | 1957 | Recrystallized from water.1 |
| PHGLOH01 | Pnma | 4.88 | 100 | 2009 | Hydrogen disorder. Private communication. |
| PHGLOH02 | Pnma | 3.57 | 100 | 2011 | Hydrogen disorder. Crystallization method not reported.2 |
| PHGLOH03 | Pnma | 4.63 | 100 | 2011 | Hydrogen disorder. Cocrystallization of 2,4,6-trihydroxybenzoic acid and benzamide (phloroglucinol is the main impurity in commercially available 2,4,6-trihydroxybenzoic acid).3 |
| PHGLOH04 | Pnma | 3.73 | 293 | 2012 | Hydrogen disorder. Slow cooling crystallization from water.4 |
| PHGLOL | P212121 | 7.5 | 295 | 1965 | Sublimation under vacuum.5 |
| PHGLOL01 | P212121 | 2.65 | 105 | 2008 | Crystallization method not reported.6 |
1. S. C. Wallwork and H. M. Powell, Acta Crystallographica, 1957, 10, 48-52.
2. L. H. Thomas, G. A. Craig, C. A. Morrison, A. M. Reilly and C. C. Wilson, Crystal Growth & Design, 2011, 11, 2045-2049.
3. C. C. Seaton and A. Parkin, Crystal Growth & Design, 2011, 11, 1502-1511.
4. D. E. Braun, D. A. Tocher, S. L. Price and U. J. Griesser, Journal of Physical Chemistry B, 2012, 116, 3961-3972.
5. K. Maartmann-Moe, Acta Crystallographica, 1965, 19, 155-157.
6. C. H. Gorbitz, M. Kaboli, M. L. Read and K. Vestli, Acta Crystallographica Section E, 2008, 64, o2023.