Organic Fluorine as a Hydrogen-Bond Acceptor: Recent Examples and Applications
Why this work is in the frame
A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.
Bibliographic record
Abstract
For more than three decades, the ability of a fluorine atom involved in a C–F bond to act as a hydrogen-bond acceptor has been a controversial issue. Throughout the years, more and more evidence has been published to support this hypothesis and it is now difficult to doubt the existence of the hydrogen bond with organic fluorine. However, since this interaction has low binding energies, it is sometimes difficult to clearly demonstrate its presence or effect in a system. In the present review, only the most recent examples from the literature are presented and the different techniques used to prove the presence of these C–F···H–X hydrogen bonds are compared and discussed according to the accepted criteria for hydrogen bonding detailed by a recent IUPAC committee. Even with its weak interaction energy, hydrogen bonds to organic fluorine have the potential to affect properties of practical systems in different spheres of chemistry. All the recent examples of such effects are highlighted. 1 Introduction 2 Properties 3 C(sp<sup>2</sup>)–F 3.1 O–H as Donor 3.2 N–H as Donor 3.3 C(sp<sup>2</sup>)–H as Donor 3.4 C(sp<sup>3</sup>)–H as Donor 4 C(sp<sup>3</sup>)–F 4.1 O–H as Donor 4.2 N–H as Donor 4.3 C(sp<sup>2</sup>)–H as Donor 4.4 C(sp<sup>3</sup>)–H as Donor 5 Conclusion
Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.
Full frame distilled prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.001 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.016 | 0.001 |
Machine scores (provisional)
The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.
Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it